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Here is a chemical reaction formula: Reactants are:m1_m2:C(C1CO1)OCCCCOCC1CO1;m1_m2:C(C#C)O, Reagents are:, and Products are 0:C(C#C)OCC(COCCCCOCC(COCC#C)O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Analogous to Example 1, 475 g 1,4-diglycidyloxybutane was reacted with 528 g of propargyl alcohol to give 1,4-bis(3-propargyloxy-2-hydroxypropyl) oxybutane. |
Here is a chemical reaction formula: Reactants are:m2_m4_m3:CO;m2_m4_m3:[OH-].[Na+];m1:N1=CC(=CC=C1)CNC1C2=C(OCC3=C1C=CC=C3)C=CC(=C2)C(=O)OCC, Reagents are:m2_m4_m3:O, and Products are 0:N1=CC(=CC=C1)CNC1C2=C(OCC3=C1C=CC=C3)C=CC(=C2)C(=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Compound 9a, 3.9 g, obtained in Example 1 was heated to reflux for an hour in a solvent mixture of 200 ml of methanol, 50 ml of water and 10 ml of 10N sodium hydroxide aqueous solution. The solvent was distilled off under reduced pressure and 4N hydrochloric acid aqueous solution was added to the residue to adjust pH to 7. After concentrating under reduced pressure, the residue was subjected to high porous polymer (HP-10; manufactured by Mitsubishi Chemical Industry Co., Ltd.) column chromatography (eluting solvent; methanol) to give 2.5 g of the crude product. The crude product was recrystallized from water to give 2.0 g of the desired product. |
Here is a chemical reaction formula: Reactants are:m2_m3:ClC\C=C/1\C2=C(OCC3=C1C=CC=C3)C=CC(=C2)C(=O)OC;m2_m3:[N+](=O)([O-])C1=CC2=C(N=CN2)C=C1, Reagents are:, and Products are 0:[N+](=O)([O-])C1=CC2=C(N(C=N2)C\C=C/2\C3=C(OCC4=C2C=CC=C4)C=CC(=C3)C(=O)OC)C=C1;0:[N+](=O)([O-])C=1C=CC2=C(N(C=N2)C\C=C/2\C3=C(OCC4=C2C=CC=C4)C=CC(=C3)C(=O)OC)C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Compound h, 2.0 g, and 5.2 g of 5-nitrobenzimidazole were treated in a manner similar to Example 23 to give a 1:1 mixture of Compounds E-55a and E-56a. The mixture was separated and purified by silica gel column chromatography (eluting solvent, hexane:ethyl acetate:triethylamine=10:10:1) to give 1.1 g of methyl (E)-11-[2-(5-nitro-1-benzimidazolyl)ethylidene]-6,11-dihydrodibenz[b,e]oxepin-2-carboxylate (Compound E-55a) and 0.7 g of methyl (E)-11-[2-(6-nitro-1-benzimidazolyl)ethylidene]-6,11-dihydrodibenz[b,e]oxepin-2-carboxylate (Compound E-56a). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:OC1C2=C(OCC3=C1C=CC=C3)C=CC(=C2)C(=O)OC;m1_m2_m3:O.O.C1(=CC=CC=C1)S(=O)[O-].[Na+];m1_m2_m3:FC(C(=O)OC(C(F)(F)F)=O)(F)F, Reagents are:, and Products are 0:C1(=CC=CC=C1)S(=O)(=O)C1C2=C(OCC3=C1C=CC=C3)C=CC(=C2)C(=O)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Compound b, 10 g, 15 g of sodium benzenesulfinate dihydrate and 25 ml of trifluoroacetic anhydride were treated in a manner similar to Example 109 to give 14.3 g of the objective compound. |
Here is a chemical reaction formula: Reactants are:m3_m2:N1C=NC=C1;m1:ClCC(=O)NC1C2=C(OCC3=C1C=CC=C3)C=CC(=C2)C(=O)OC, Reagents are:m3_m2:C1(=CC=CC=C1)C, and Products are 0:N1(C=NC=C1)CC(=O)NC1C2=C(OCC3=C1C=CC=C3)C=CC(=C2)C(=O)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Crude methyl 11-chloroacetamido-6,11-dihydrodibenz[b,e]oxepin-2-carboxylate, 3.0 g, was heated to reflux for 4 hours in 100 ml of toluene together with 0.9 g of imidazole. After allowing to cool, the solvent was distilled off under reduced pressure. The obtained residue was extracted with 300 ml of methylene chloride. The extract was washed successively with saturated sodium bicarbonate aqueous solution and saturated sodium chloride aqueous solution. After drying over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluting solvent; chlororform:methanol=10:1) to give 1.6 g of the product. |
Here is a chemical reaction formula: Reactants are:m1_m2:N1=CC=CC=C1;m1_m2:[H-].[Al+3].[Li+].[H-].[H-].[H-];m4_m3:ClC\C=C/1\C2=C(OCC3=C1C=CC=C3)C=CC(=C2)C(=O)OC, Reagents are:m4_m3:O1CCCC1, and Products are 0:N1=CC(=CC=C1)C\C=C/1\C2=C(OCC3=C1C=CC=C3)C=CC(=C2)C(=O)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To 50 ml of pyridine was added to 2.0 g of lithium aluminum hydride, and the mixture was stirred at room temperature for one night. Then, 90 ml of tetrahydrofuran solution containing 5.0 g of Compound h was dropwise added thereto under ice-cooling. The mixture was stirred at room temperature for 5 hours, and the solvent was distilled off under reduced pressure. The residue was washed with tetrahydrofuran, and the washings were concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (eluting solvent; hexane:ethyl acetate:triethylamine=10:10:1) to give 1.7 g of the desired product. |
Here is a chemical reaction formula: Reactants are:m1_m2_m5:CN1CCNCC1;m1_m2_m5:C=O;m4_m6:C=C1C(C=CC=2OCC3=C(CC21)C=CC=C3)C(=O)OC;m3:FC(C(=O)O)(F)F, Reagents are:m1_m2_m5:ClCC(Cl)(Cl)Cl;m4_m6:ClCC(Cl)(Cl)Cl, and Products are 0:CN1CCN(CC1)CC=C1C2=C(OCC3=C1C=CC=C3)C=CC(=C2)C(=O)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1-Methylpiperazine, 30 ml, and 74 g of paraformaldehyde were dissolved in 2 l of tetrachloroethane and 100 ml of trifluoroacetic acid was dropwise added to the solution. After stirring at 60° C. for 2 hours, a solution of 36 g of methyl 1-methylene-6,11-dihydrodibenz[b,e]oxepin-2-carboxylate in 600 ml of tetrachloroethane was dropwise added to the reaction mixture followed by stirring at 90° C. for further 3 hours. The reaction mixture was concentrated to dryness under reduced pressure and 4 N hydrochloric acid aqueous solution was added to the residue to adjust pH to 1. Then, the mixture was washed with diethyl ether. Thereafter, 10 N sodium hydroxide aqueous solution was added to adjust pH to 13. Extraction was performed with 3 l of methylene chloride. After washing with saturated sodium chloride aqueous solution and drying over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluting solvent; hexane: ethyl acetate: triethylamine=5:5:1) to give 44 g of colorles oily methyl 11-[2-(4-methyl-1-piperazinyl)ethylidene]-6,11-dihydrodibenz[b,e]oxepin-2-carboxylate. |
Here is a chemical reaction formula: Reactants are:m1:OC1C2=C(OCC3=C1C=CC=C3)C=CC(=C2)C(=O)OC;m3:SCCO;m2:FC(C(=O)OC(C(F)(F)F)=O)(F)F, Reagents are:m4:C(Cl)Cl;m5:C(Cl)Cl, and Products are 0:OCCSC1C2=C(OCC3=C1C=CC=C3)C=CC(=C2)C(=O)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: In 400 ml of methylene chloride was suspended 40.0 g of Compound b obtained in Reference Example 2. Trifluoroacetic anhydride, 21.0 ml, was added to the suspension followed by stirring at room temperature for an hour. Them, 10.7 ml of 2-mercaptoethanol was added to the mixture followed by stirring for further 4 hours. After 100 ml of methylene chloride was added to the reaction mixture, the mixture was washed with saturated aqueous sodium chloride solution. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The obtained crude product was recrystallized from toluene to give 37.6 g of methyl 11-(2-hydroxyethyl)thio-6,11-dihydrodibenz[b,e]oxepin-2-carboxylate as white crystals. |
Here is a chemical reaction formula: Reactants are:m2:C(CCC)[Li].CCCCCC;m1_m5:BrC=1C=CC2=C(OCC3=C(C2OC)C=CC=C3)C1;m3:C(=O)=O;m6_m4:S(O)(O)(=O)=O, Reagents are:m1_m5:O1CCCC1;m6_m4:CO, and Products are 0:COC1C2=C(OCC3=C1C=CC=C3)C=C(C=C2)C(=O)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 3-Bromo-11-methoxy-6,11-dihydrodibenz[b,e]oxepine, 30 g, was dissolved in 500 ml of tetrahydrofuran. After cooling to -78° C., 65 ml of 1.6 N n-butyl lithium/hexane solution was dropwise added to the solution in a nitrogen atmosphere followed by stirring at -78° C. for further 40 minutes. The reaction solution was dropwise added onto 100 g of dry ice, which was allowed to stand to elevate to room temperature. The solvent was distilled off under reduced pressure. To the residue obtained, were added 500 ml of methanol and 10 ml of conc. sulfuric acid. The mixture was heated to reflux for 2 hours. After allowing to cool, the solvent was distilled off under reduced pressure. The residue was extracted with 500 ml of ethyl acetate. After washing successively with saturated sodium chloride aqueous solution, saturated sodium bicarbonate aqueous solution and saturated sodium chloride aqueous solution, the extract was dried over anhydrous magnesium sulfate. The solvent was the distilled off under reduced pressure. The residue was subjected to silica gel column chromatography (eluting solvent; hexane: ethyl acetate=1:1) to give 19.3 g of the product as pale yellow oil. |
Here is a chemical reaction formula: Reactants are:m4:ClCCOCCOCCO;m1_m2_m3:[N+](=O)([O-])C=1C=C(C=CC1)O;m1_m2_m3:CN(C=O)C;m1_m2_m3:C([O-])([O-])=O.[K+].[K+], Reagents are:m6_m5:O;m6_m5:C(C)(=O)OCC, and Products are 0:[N+](=O)([O-])C=1C=C(OCCOCCOCCO)C=CC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: While stirring a mixture of 27.8 g of m-nitrophenol, 120 ml of N,N-dimethylformamide, and 25 g of potassium carbonate at 80° C., 37 g of 2-(2-(2-chloroethoxy)ethoxy)-ethanol was added dropwise to the mixture. After stirring the mixture for one hour at 80° C., 200 ml of ethyl acetate and 200 ml of water were added to the reaction mixture and the ethyl acetate layer was extracted. The ethyl acetate layer was washed with 200 ml of water and concentrated to remove ethyl acetate to provide 2-(2-(2-(3-nitrophenoxy)ethoxy)ethoxy)ethanol (1-A). |
Here is a chemical reaction formula: Reactants are:m6_m5:O;m4:C(C(=C)C)(=O)Cl;m1_m2_m3:BrC=1SC=C(C1)COCCO;m1_m2_m3:N1=CC=CC=C1;m1_m2_m3:C(C)#N, Reagents are:m6_m5:C(C)(=O)OCC, and Products are 0:C(C(=C)C)(=O)OCC(OC)C=1C=C(SC1)Br, please give me the reaction condition of this formula. | The condition of this chemical reaction is: While stirring a mixture of 0.1 mol of 2-bromo-4-2-hydroxyethoxymethylthiophene, 0.1 mol of pyridine, and 100 ml of acetonitrile at a temperature of lower than 10° C., 0.1 mol of methacryloyl chloride was added dropwise to the mixture over a period of 30 minutes. After stirring the mixture for one hour, 200 ml of ethyl acetate and 200 ml of water were added to the mixture. The ethyl acetate layer was extracted, concentrated, and purified by column chromatography to provide 22.1 g of 2-bromo-4-thienyl-methoxyethyl methacrylate (5-A). |
Here is a chemical reaction formula: Reactants are:m2_m3_m4:C(C1=CC=CC=C1)C(=O)CC1=CC=CC=C1;m2_m3_m4:C(C=CC1=CC=CC=C1)=O;m2_m3_m4:C(C)NCC, Reagents are:m5:C(C)O, and Products are 0:C1(=CC=CC=C1)C1=C(C(=CC=C1C1=CC=CC=C1)C1=CC=CC=C1)O;0:C1(=CC=CC=C1)C=1C(C(CCC1C1=CC=CC=C1)C1=CC=CC=C1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 2,3,6-Triphenylphenol was prepared according to A. S. Hay and R. F. Clark (Macromolecules, 3, 533, 1970). 11.36 g (54 mmoles) of dibenzylketone, 7.14 g (54 mmoles) of cinnamaldehyde and 5 mL of diethylamine were mixed and the solution became yellow and after 20 min. a yellow solid deposited. The solid was added to ethanol (80 mL), cooled and filtered to yield 2,3,6-triphenylcyclohexenone (91%). The product (8.0 g) was mixed with 1 g of 5% Pd on carbon and heated at 270° C. for 30 min and then cooled. The mixture was dissolved in hot ethylacetate and the hot solution was filtered and cooled to yield 2,3,6-triphenylphenol (69%). The oxidation of triphenylphenol (5 g) was carried out in butyronitrile (50 mL) with a CuCl catalyst (0.4 g) by passing oxygen through the stirred solution at 100° C. for 8 hours. The reaction mixture was cooled and filtered to yield (82%) of the crude biphenol. Reduction with a few drops of hydrazine in hot acetic acid reduced any of the diphenoquinone in the product to give 2,2',3,3',5,5'-hexaphenyl-[1,1'-biphenyl]-4,4'-diol which was further purified by crystallization. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:COC(=O)C1=CC=C(C=C1)CBr;m1_m2_m3:C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1, Reagents are:m1_m2_m3:C1(=CC=CC=C1)C, and Products are 0:[Br-].C(=O)(OC)C1=CC=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a 2 L 3-neck round bottom flask fitted with a glass stopper, rubber septum, and reflux condenser with a nitrogen inlet tube, was added 64.90 g (283 mmol) methyl 4-bromomethyl benzoate, 81.74 g (311 mmol) triphenylphosphine, and 744 mL toluene. The solution was heated at 80° C. for 5 h. After cooling to room temperature, the reaction vessel was placed in an ice bath. The resulting precipitate was filtered, washed with toluene, and dried in a vacuum oven to afford 126.35 g (89%) (4-carbomethoxy)benzyltriphenylphosphonium bromide as a white solid, mp.=248°-250° C.: 1H NMR (CDCl3, 200 MHz) d 3.86 (s, 3H), 5.70 (d, J=15.3 HZ, 2H), 7.24 (m, 4H), 7.71 (m, 15H). |
Here is a chemical reaction formula: Reactants are:m1_m2_m6:[Br-].C(=O)(OC)C1=CC=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1;m1_m2_m6:C(=O)C1=CC=C(C(=O)OC)C=C1;m3:C1(=CC=CC=C1)C;m4_m5:C[O-].[Na+], Reagents are:m1_m2_m6:CO;m4_m5:CO, and Products are 0:C(=O)(OC)C1=CC=C(C=C1)C=CC1=CC=C(C=C1)C(=O)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a 2 L 3-neck round bottom flask fitted with a glass stopper, rubber septum, and reflux condenser with a nitrogen inlet tube, was added 126.35 g (251 mmol) (4-carbomethoxy)benzyltriphenylphosphonium bromide, 49.45 g (302 mmol) methyl 4-formylbenzoate, and 632 mL 2:1 methanol:toluene. After the starting material dissolved, 63.2 mL (277 mmol) 25% sodium methoxide solution in methanol was added dropwise over several minutes. The reaction vessel was heated at reflux for 30 minutes. After cooling to room temperature, the reaction vessel was cooled at 0° C. for several hours. The resulting precipitate was filtered and dried in a vacuum oven to afford 59.0 g (79%) 4,4'-bis(carbomethoxy)stilbene as a 7:3 mixture of cis:trans isomers. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:OC1=CC=C(C=CC(=O)O)C=C1;m1_m2_m3:CO;m1_m2_m3:S(O)(O)(=O)=O, Reagents are:, and Products are 0:OC1=CC=C(C=CC(=O)OC)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a 250 mL round bottom flask fitted with a reflux condenser and a nitrogen inlet tube was added 20.0 g (121.8 mmol) 4-hydroxycinnamic acid, 100 mL (246.9 mmol) methanol, and 5.0 g (50.0 mmol) concentrated sulfuric acid. The reaction vessel was heated at 75°-80° C. overnight. After cooling to room temperature, the resulting solution was diluted with 150 mL distilled water, and cooled to 0° C. The resulting precipitate was filtered, washed with sat. NaHCO3 solution, and recrystallized from EtOH/water to afford 16.8 g (77%) methyl 4-hydroxycinnamate which was used without further purification: mp.=139°-140° C.; 1H NMR (CD3SOCD3, 300 MHz) δ 3.42 (broad s, 1H), 3.70 (s, 3H), 6.40 (d, J=16.0 Hz, 1H), 6.81 (d, J=8.4 Hz, 2H), 7.55 (d, J=8.4 Hz, 2H), 7.58 (d, J=16.0 Hz, 1H). |
Here is a chemical reaction formula: Reactants are:m2:C[Si](C)(C)Cl;m1:C(CCCO)O, Reagents are:m4:C[Si](C)(C)N[Si](C)(C)C;m3:C[Si](C)(C)N[Si](C)(C)C;m5:C[Si](C)(C)N[Si](C)(C)C, and Products are 0:[Si](C)(C)(C)OCCCCO[Si](C)(C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1,4-Butanediol (54 g, 0.60 mol) was placed in a 500 mL 3-necked RB flask and treated with 0.3 mL trimethylsilyl chloride. A portion of HMDS (ca. 20 mL) was added, and an exothermic reaction took place as the mixture became homogeneous. The remainder of the HMDS (120 mL, 0.66 mol total) was added at a controlled rate (ca. 3-5 mL/min), maintaining the reaction temperature at ca. 50° C. Heating was continued at 100° C. (3 h), and 150° C. (1.5 h). GC analysis (method 1) revealed excess HMDS and one product. Distillation provided 127.8 g of colorless oil, bp 97°-99° C./15 mm. 1H NMR (CDCl3): 3.75-3.50 (m, 4H), 1.75-1.50 (m, 4H), 0.16 (s, 18H). |
Here is a chemical reaction formula: Reactants are:m2:C[Si](C)(C)Cl;m1:C(CCCCO)O, Reagents are:m5:C[Si](C)(C)N[Si](C)(C)C;m4:C[Si](C)(C)N[Si](C)(C)C;m3:C[Si](C)(C)N[Si](C)(C)C, and Products are 0:[Si](C)(C)(C)OCCCCCO[Si](C)(C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1,5-Pentanediol (65 g, 0.62 mol) was placed in a 500 mL 3-necked RB flask and treated with 0.4 mL trimethylsilyl chloride. A portion of HMDS (ca. 20 mL) was added, and an exothermic reaction took place as the mixture became homogeneous. The remainder of the HMDS (130 mL, 0.71 mol total) was added at a controlled rate (ca. 3-5 mL/min), maintaining the reaction temperature at ca. 50° C. Heating was continued at 100° C. (1 h), and 150° C. (2.5 h). GC analysis (method 1) revealed excess HMDS and one product. Distillation provided 139 g of colorless oil, bp 47°-49° C./0.1 mm. 1H NMR (CDCl3): 3.60 (t, J=7Hz, 4H), 1.57 (m, 4H), 1.40 (m, 2H), 0.12 (s, 18H), consistent with the assigned structure. |
Here is a chemical reaction formula: Reactants are:m2:C[Si](C)(C)Cl;m1:C(C(C)O)O, Reagents are:m4:C[Si](C)(C)N[Si](C)(C)C;m5:C[Si](C)(C)N[Si](C)(C)C;m3:C[Si](C)(C)N[Si](C)(C)C, and Products are 0:[Si](C)(C)(C)OC(C)CO[Si](C)(C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1,2-Propanediol (58.8 g, 0.77 mol) was placed in a 500 mL 3-necked RB flask and treated with 0.2 mL trimethylsilyl chloride. A small volume of HMDS (ca. 10 mL) was added, and an exothermic reaction took place as the mixture became homogeneous. The remainder of the HMDS (170 mL) was added at a controlled rate (ca. 3-5 mL/min), maintaining the reaction temperature at ca. 50°-70° C. Heating was continued at 100° C. (1.5 h), 120° C. (1.0 h),and 140° C. (2.5 h). GC analysis (method 1) revealed excess HMDS and one product. Distillation provided 147 g of colorless oil, bp 70°-72° C./10 mm. 1H NMR (CDCl3): 3.83 (m, 1H), 3.50 and 3.38 (AB pattern with additional coupling, 2H), 1.15 (d, J=7 Hz, 3H), 0.15 (partially resolved singlets, 18H). |
Here is a chemical reaction formula: Reactants are:m5:C(C)(C)N(CC)C(C)C;m4:C[N+]1(C[C@H](CC1)S)C;m3:O[C@H](C)[C@@H]1[C@@H]2N(C(C(C2)=O)C(=O)OCC2=CC=C(C=C2)[N+](=O)[O-])C1=O;m1_m2:C(C)(C)N(CC)C(C)C;m1_m2:C1(=CC=CC=C1)P(=O)(C1=CC=CC=C1)Cl, Reagents are:m7:C(C)#N;m6:C(C)#N, and Products are 0:C[N+]1(C[C@H](CC1)SC=1C[C@H]2N(C1C(=O)[O-])C([C@@H]2[C@@H](C)O)=O)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 183 μl of diisopropylethylamine and 218 μl of diphenylphosphoryl chloride were simultaneously added, whilst ice-cooling, to a solution of 348 mg of 4-nitrobenzyl (5R, 6S)-6-[(1R)-1-hydroxyethyl]-2-oxo-1-carbapenam-3-carboxylate dissolved in 4 ml of dry acetonitrile and the mixture was stirred at the same temperature for 1 hour. At the end of this time, a solution of 338 mg of the crude (3S)-1,1-dimethyl-3-mercaptopyrrolidinium salt prepared as described in Example 5-(1) in 4 ml of dry acetonitrile and 209 μl of diisopropylethylamine were added to the mixture, whilst ice-cooling. The mixture was then allowed to stand at the same temperature for 1 hour and then for two days in a refrigerator. At the end of this time, the reaction mixture was washed by decantation with diethyl ether. The resulting product was dissolved in a mixture of 30 ml of tetrahydrofuran and 30 ml of a 0.1M phosphate buffer (pH 7.0) and hydrogenated at room temperature for 2.5 hours in the presence of 400 mg of 10% w/w palladium-on-charcoal. At the end of this time, an insoluble material was removed by filtration and the filtrate was washed with diethyl ether. The aqueous layer was concentrated by evaporation under reduced pressure and then subjected to column chromatography through Diaion HP-20AG (Mitsubishi Chemical Industries, Inc.). The title compound was prepared as a crude product from the fractions eluted with water. The crude compound was then further purified by chromatography through a Lobar column (Merck Co. LiChroprep RP-8, size B) and the fractions eluted with 5% by volume aqueous methanol were collected, concentrated by evaporation under reduced pressure and lyophilized to afford 60 mg of the title compound. |
Here is a chemical reaction formula: Reactants are:m1:O[C@H](C)[C@@H]1[C@@H]2N(C(C(C2)=O)C(=O)OCC2=CC=C(C=C2)[N+](=O)[O-])C1=O;m2:CN(C(=O)[C@H]1[N+](C[C@H](C1)S)(C)CC)C, Reagents are:, and Products are 0:C(C)[N+]1([C@@H](C[C@@H](C1)SC=1C[C@H]2N(C1C(=O)[O-])C([C@@H]2[C@@H](C)O)=O)C(N(C)C)=O)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Following a procedure similar to that described in Example 6, but using 459 mg of 4-nitrobenzyl (5R, 6S)-6-[(1R)-1-hydroxyethyl]-2-oxo-1-carbapenam-3-carboxylate and 580 mg of the crude (2S, 4S)-2-(N,N-dimethylcarbamoyl)-1-ethyl-1-methyl-4-mercaptopyrrolidinium salt [prepared as described in Example 9-(2)], 55 mg of the title compound were obtained. |
Here is a chemical reaction formula: Reactants are:m1_m2:C(C)(C)N(CC)C(C)C;m1_m2:C1(=CC=CC=C1)P(=O)(C1=CC=CC=C1)Cl;m3:O[C@H](C)[C@@H]1[C@@H]2N(C(C(C2)=O)C(=O)OCC2=CC=C(C=C2)[N+](=O)[O-])C1=O;m4:C(N)(=O)[C@H]1[N+](C[C@H](C1)S)(C)C, Reagents are:m6:C(C)OCC;m5:C(C)#N, and Products are 0:C(N)(=O)[C@H]1[N+](C[C@H](C1)SC=1C[C@H]2N(C1C(=O)[O-])C([C@@H]2[C@@H](C)O)=O)(C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 210 μl of diisopropylethylamine and 250 μl of diphenylphosphoryl chloride were simultaneously added, whilst ice-cooling, to a solution of 400 mg of 4-nitrobenzyl (5R, 6S)-6-[(1R)-1-hydroxyethyl]-2-oxo-1-carbapenam-3-carboxylate dissolved in 5 ml of dry acetronitrile, and the mixture was stirred for 1 hour, whilst ice-cooling. At the end of this time, a solution of 447 mg of the crude (2S, 4S)-2-carbamoyl-1,1-dimethyl-4-mercaptopyrrolidinium salt prepared as described in Example 1-(1) in 5 ml of dry acetonitrile was added to the mixture, whilst ice-cooling, and then the mixture was allowed to stand for 4 hours at the same temperature and then for 2 days in a refrigerator. The reaction mixture was then poured into diethyl ether and the resulting deposit was washed repeatedly by decantation. The crude product was dissolved in a mixture of 30 ml of tetrahydrofuran and 30 ml of a 0.1M phosphate buffer (pH 7.0) and hydrogenated at room temperature for 2.5 hours in the presence of 450 mg of 10% w/w palladium-on-charcoal. At the end of this time, insoluble materials were removed by filtration using a Celite filter aid. The aqueous layer was concentrated by evaporation under reduced pressure, and the residue was transferred to a column packed with Diaion HP-20AG (Mitsubishi Chemicals Industries, Ltd.). Fractions eluted with water were collected and lyophilized to afford the title compound as a powder. This was further purified using a Lobar column (Merck, LiChroprep RP-8 size B) and fractions eluted with a 5% by volume aqueous methanolic solution were collected and concentrated by evaporation under reduced pressure followed by lyophilization, to afford 208 mg of the title compound. |
Here is a chemical reaction formula: Reactants are:m1_m4_m2_m3:CC1=C(OC(O1)=O)CI;m1_m4_m2_m3:O=C1NCCC1SC=1[C@@H]([C@H]2N(C1C(=O)[O-])C([C@@H]2[C@@H](C)O)=O)C.[Na+];m1_m4_m2_m3:CN(C=O)C, Reagents are:m5:C(C)(=O)OCC;m1_m4_m2_m3:C(Cl)(Cl)Cl, and Products are 0:O=C1NCCC1SC=1[C@@H]([C@H]2N(C1C(=O)OCC=1OC(OC1C)=O)C([C@@H]2[C@@H](C)O)=O)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 66 mg of 5-methyl-2-oxo-1,3-dioxolen-4-ylmethyl iodide (prepared by heating 5-methyl-2-oxo-1,3-dioxolen-4-ylmethyl bromide and sodium iodide under reflux in acetone) in chloroform was added to a mixture of 47.6 mg of sodium (1R, 5S, 6S)-2-(2-oxo-3-pyrrolidinylthio)-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate and 0.4 ml of dry dimethylformamide. The mixture was stirred at room temperature for 80 minutes and then at 30°-45° C. for 4.5 hours. At the end of this time, the reaction mixture was diluted with ethyl acetate and washed four times with an aqueous solution of sodium chloride. The extract was dried and the solvent was distilled off under reduced pressure. The residue was purified by Lobar column chromatography (Merck, LiChroprep Si60, size A), eluted with a 10:1 by volume mixture of ethyl acetate and methanol, to give 27.4 mg of the title compound in the form of a colorless powder. |
Here is a chemical reaction formula: Reactants are:m2:C1(CCCCC1)OC(=O)OC(C)I;m1:O=C1NCC(C1)SC=1C([C@H]2N(C1C(=O)[O-])C(C2[C@@H](C)O)=O)C.[Na+], Reagents are:, and Products are 0:O=C1NCC(C1)SC=1[C@@H]([C@H]2N(C1C(=O)OC(C)OC(=O)OC1CCCCC1)C([C@@H]2[C@@H](C)O)=O)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Following a procedure similar to that described in Example 39, but using 54 mg of sodium 2-(2-oxo-4-pyrrolidinylthio)-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate obtained by a similar procedure to that described in Example 36 and 50 μl of 1-(cyclohexyloxycarbonyloxy)ethyl iodide, 62 mg of the title compound were obtained as a colorless powder. |
Here is a chemical reaction formula: Reactants are:m2:CC1=C(OC(O1)=O)CBr;m1:O=C1NCC(C1)SC=1C([C@H]2N(C1C(=O)[O-])C(C2[C@@H](C)O)=O)C.[Na+], Reagents are:, and Products are 0:O=C1NCC(C1)SC=1[C@@H]([C@H]2N(C1C(=O)OCC=1OC(OC1C)=O)C([C@@H]2[C@@H](C)O)=O)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Following a procedure similar to that described in Example 39, but using 50 mg of sodium 2-(2-oxo-4-pyrrolidinylthio)-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate and 55 mg of 5-methyl-2-oxo-1,3-dioxolen-4-ylmethyl bromide, 50 mg of the title compound were obtained as a colorless powder. |
Here is a chemical reaction formula: Reactants are:m3:[OH-].[NH4+];m4:[Cl-].[NH4+];m1:C(C)(C)(C)OC(=O)N1[C@@H](C[C@H](C1)O)C(=O)O;m2_m6:ClC(=O)OCC, Reagents are:m7:C(C)N(CC)CC;m5:O1CCCC1;m2_m6:O1CCCC1, and Products are 0:C(C)(C)(C)OC(=O)N1[C@@H](C[C@H](C1)O)C(N)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 58 g of (2S, 4R)-1-(t-butoxycarbonyl)-4-hydroxy-2-pyrrolidinecarboxylic acid [prepared as described in step (1) aboveπ were dissolved in 850 ml of dry tetrahydrofuran, and then 38.2 ml of triethylamine were added to the mixture at -15° to -20° C. A solution of 26.3 ml of ethyl chloroformate in 240 ml of dry tetrahydrofuran was then added dropwise to the mixture at -15° to -20° C., and the mixture was stirred at the same temperature for 35 minutes. At the end of this time, 258 ml of 28% w/v aqueous ammonium hydroxide were added to the mixture at -15° to -20° C., and the mixture was allowed to stand overnight at room temperature. Ammonium chloride was then added to the reaction mixture, which was then extracted with tetrahydrofuran. The extract was dried and freed from the solvent by distillation under reduced pressure. The resulting residue was triturated with diethyl ether to cause crystallization. The crystals were collected by filtration and washed with diethyl ether to afford 49.7 g of the title compound as colorless crystals, melting at 146°-148° C. |
Here is a chemical reaction formula: Reactants are:m2_m5:C(C)(C)(C)OC(=O)N1[C@@H](C[C@H](C1)O)C(N)=O;m1:CS(=O)(=O)Cl;m3:C(C)N(CC)CC;m4:[Cl-].[Na+], Reagents are:m2_m5:O1CCCC1, and Products are 0:C(C)(C)(C)OC(=O)N1[C@@H](C[C@H](C1)OS(=O)(=O)C)C(N)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1.85 ml of methanesulfonyl chloride was added, whilst ice-cooling, to a solution of 5.0 g of (2S, 4R)-1-(t-butoxycarbonyl)-2-carbamoyl-4-hydroxypyrrolidine [prepared as described in step (2) above] in 250 ml of dry tetrahydrofuran, followed by 3.31 ml of triethylamine. The mixture was then stirred at 0° to 5° C. for 1 hour, after which it was poured into an aqueous solution of sodium chloride and extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The residue was purified by chromatography through silica gel (eluted with a 9:1 by volume mixture of ethyl acetate and methanol) to afford 5.5 g of the title compound as colorless crystals. |
Here is a chemical reaction formula: Reactants are:m4:C([O-])(O)=O.[Na+];m1_m5:C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](C1)SCC1=CC=C(C=C1)OC)C(N)=O;m2_m3:O1CCOCC1;m2_m3:Cl, Reagents are:m1_m5:C(C)(=O)OCC, and Products are 0:C(N)(=O)[C@H]1NC[C@H](C1)SCC1=CC=C(C=C1)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1.92 g of (2S, 4S)-1-(t-butoxycarbonyl)-2-carbamoyl-4-(4-methoxybenzylthio)pyrrolidine [prepared as described in step (4) above] was dissolved in 25 ml of ethyl acetate, and 26.2 ml of a 4N dioxane solution of hydrogen chloride were added to the solution, whilst ice-cooling. The mixture was then stirred at 0° to 5° C. for 2 hours and at room temperature for 30 minutes. At the end of this time, it was poured into a saturated aqueous solution of sodium bicarbonate, to make it weakly basic, and was extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, to give 1.36 g of the title compound as a powder, melting at 120°-121° C. |
Here is a chemical reaction formula: Reactants are:m7_m1:C(C)(C)(C)OC(=O)N1[C@@H](C[C@H](C1)O)C(=O)O;m2_m6:ClC(=O)OCC;m3:CN;m4:[Cl-].[Na+], Reagents are:m7_m1:C(C)N(CC)CC;m2_m6:O1CCCC1;m5:O1CCCC1, and Products are 0:C(C)(C)(C)OC(=O)N1[C@@H](C[C@H](C1)O)C(NC)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 9.91 ml of triethylamine were added at -40° C. to a solution of 15.03 g of (2S, 4R)-1-(t-butoxycarbonyl)-4-hydroxy-2-pyrrolidinecarboxylic acid dissolved in 250 ml of dry tetrahydrofuran, and then a solution of 6.81 ml of ethyl chloroformate in 30 ml of dry tetrahydrofuran was added at -30° to -40° C. to the resulting mixture, which was then stirred at the same temperature for 1 hour, 16.82 ml of a 40% by volume aqueous methylamine solution were then added at -30° C., and the temperature of the reaction mixture was allowed to rise to room temperature; the reaction was then allowed to continue for 1 hour. At the end of this time, the reaction mixture was mixed with a small amount of an aqueous solution of sodium chloride and extracted thrice with ethyl acetate. The combined extracts were washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, giving 12.76 g of the title compound as a colorless oil. |
Here is a chemical reaction formula: Reactants are:m3:CS(=O)(=O)Cl;m1:C(C)N(CC)CC;m4:[Cl-].[Na+];m2:C(C)(C)(C)OC(=O)N1[C@@H](C[C@H](C1)O)C(NC)=O, Reagents are:m5:O1CCCC1, and Products are 0:C(C)(C)(C)OC(=O)N1[C@@H](C[C@H](C1)OS(=O)(=O)C)C(NC)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 7.11 ml of triethylamine were added, whilst ice-cooling, to a solution of 11.29 g of (2S, 4R)-1-(t-butoxycarbonyl)-2-methylcarbamoyl-4-hydroxypyrrolidine [prepared as described in step (1) above] dissolved in 120 ml of dry tetrahydrofuran, and then 3.93 ml of methanesulfonyl chloride were added to the resulting mixture, and the mixture was stirred at 0° to 5° C. for 30 minutes and then at 15° C. for 30 minutes. It was then poured into an aqueous solution of sodium chloride and extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, giving 11.58 g of the title compound as colorless crystals. |
Here is a chemical reaction formula: Reactants are:m2:COC1=CC=C(CS)C=C1;m4:[Cl-].[Na+];m1:[H-].[Na+];m3_m6:C(C)(C)(C)OC(=O)N1[C@@H](C[C@H](C1)OS(=O)(=O)C)C(NC)=O, Reagents are:m5:O1CCCC1;m3_m6:CN(C=O)C, and Products are 0:C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](C1)SCC1=CC=C(C=C1)OC)C(NC)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1.80 g of sodium hydride (as a 55% w/w dispersion in mineral oil) was added, whilst ice-cooling, to a solution of 5.70 ml of 4-methoxybenzyl mercaptan dissolved in 100 ml of dry tetrahydrofuran, and the mixture was then stirred at 0° to 5° C. for 30 minutes. At the end of this time, a solution of 11.00 g of (2S, 4R)-1-(t-butoxycarbonyl)-4-methanesulfonyloxy-2-methylcarbamoylpyrrolidine [prepared as described in step (2) above] in 80 ml of dry dimethylformamide was added to the mixture, and the mixture was stirred at 34° C. for 4.5 hours. The reaction mixture was then poured into an aqueous solution of sodium chloride and extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure. The residue was purified by column chromatography through silica gel (eluted with a 5:1 by volume mixture of ethyl acetate and hexane) to afford 4.35 g of the title compound as an oil. |
Here is a chemical reaction formula: Reactants are:m1_m2:O1CCOCC1;m1_m2:Cl;m3:C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](C1)SCC1=CC=C(C=C1)OC)C(NC)=O;m4:C([O-])(O)=O.[Na+], Reagents are:m5:C(C)(=O)OCC, and Products are 0:COC1=CC=C(CS[C@H]2C[C@H](NC2)C(NC)=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 52.5 ml of a 4N dioxane solution of hydrogen chloride were added, whilst ice-cooling, to a solution of 4.00 g of (2S, 4S)-1-(t-butoxycarbonyl)-4-(4-methoxybenzylthio)-2-methylcarbamoylpyrrolidine [prepared as described in step (3) above] dissolved in 50 ml of ethyl acetate. The mixture was stirred at 0° to 50° C. for 30 minutes and then at room temperature for 2 hours. At the end of this time, the reaction mixture was poured into a saturated aqueous solution of sodium bicarbonate to make it weakly basic, and it was then extracted with ethyl acetate. The aqueous layer was saturated with ammonium chloride and then extracted with tetrahydrofuran. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography through silica gel (eluted with a 5:1 mixture by volume of ethyl acetate and methanol), to afford 2.34 g of the title compound as colorless crystals, melting at 53°-54° C. |
Here is a chemical reaction formula: Reactants are:m3:COC1=CC=C(CS[C@H]2C[C@H](NC2)C(NC)=O)C=C1;m4:[Cl-].[Na+];m1_m2:CI;m1_m2:C([O-])(O)=O.[Na+], Reagents are:m5:CN(C=O)C, and Products are 0:COC1=CC=C(CS[C@H]2C[C@H](N(C2)C)C(NC)=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 244 μl of methyl iodide and 300 mg of sodium bicarbonate were added, whilst ice-cooling, to a solution of 1.00 g of (2S, 4S)-4-(4-methoxybenzylthio)-2-methylcarbamoylpyrrolidine [prepared as described in step (4) above] dissolved in 6 ml of dry dimethylformamide. The mixture was then stirred at 0° to 5° C. for 1 hour and allowed to stand overnight at room temperature. At the end of this time, the reaction mixture was poured into an aqueous solution of sodium chloride and extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, and the residue was purified by column chromatography through silica gel (eluted with a 10:1 by volume mixture of ethyl acetate and methanol), to afford 222 mg of the title compound as colorless crystals, melting at 82°-84° C. |
Here is a chemical reaction formula: Reactants are:m2:COC1=CC=C(CS[C@H]2C[C@H](N(C2)C)C(NC)=O)C=C1;m1:FS(=O)(=O)OC, Reagents are:m3:C(Cl)Cl, and Products are 0:S(=O)(=O)([O-])F.C[N+]1([C@@H](C[C@@H](C1)SCC1=CC=C(C=C1)OC)C(NC)=O)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 280 μl of methyl fluorosulfonate were added, whilst ice-cooling, to a solution of 210 mg of (2S, 4S)-4-(4-methoxybenzylthio)-1-methyl-2-methylcarbamoylpyrrolidine [prepared as described in step (5) above] dissolved in 30 ml of dry methylene chloride. The mixture was stirred at the same temperature for 30 minutes and then at room temperature for 5 hours. At the end of this time, the solvent was removed by distillation under reduced pressure, and the residue was washed repeatedly by decantation with diethyl ether and dried under reduced rpessure, to afford 281 mg of the title compound as a colorless powder. |
Here is a chemical reaction formula: Reactants are:m4:Cl;m7_m1:C(C)(C)(C)OC(=O)N1[C@@H](C[C@H](C1)O)C(=O)O;m2_m6:ClC(=O)OCC;m3:CNC, Reagents are:m5:O1CCCC1;m7_m1:C(C)N(CC)CC;m2_m6:O1CCCC1, and Products are 0:C(C)(C)(C)OC(=O)N1[C@@H](C[C@H](C1)O)C(N(C)C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 3.84 ml of triethylamine was added, at -15° to -20° C., to a solution of 5.8 g of (2S, 4R)-1-(t-butoxycarbonyl)-4-hydroxy-2-pyrrolidinecarboxylic acid dissolved in 85 ml of dry tetrahydrofuran, and then a solution of 2.63 ml of ethyl chloroformate in 25 ml of dry tetrahydrofuran was added to the resulting mixture at the same temperature. The reaction mixture was then stirred for 2 hours, after which 19.75 ml of 50% by volume aqueous dimethylamine was added to it at -20° to -25° C. The mixture was then stirred for 3 hours under ice cooling, after which is was allowed to stand overnight at room temperature. At the end of this time, the mixture was poured into a mixture of 30 ml of concentrated hydrochloric acid and ice and extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried. The solvent was then removed by distillation under reduced pressure, and the residue was purified by column chromatography through silica gel (eluted with a 9:1 by volume mixture of ethyl acetate and methanol) to afford 429 mg of the title compound. |
Here is a chemical reaction formula: Reactants are:m3:C(C)(C)(C)OC(=O)N1[C@@H](C[C@H](C1)OS(=O)(=O)C)C(N(C)C)=O;m2:COC1=CC=C(CS)C=C1;m1:[OH-].[Na+], Reagents are:m4:CN(C=O)C, and Products are 0:C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](C1)SCC1=CC=C(C=C1)OC)C(N(C)C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 151 mg of sodium hydroxide (as a 55% w/w dispersion in mineral oil) were added, whilst ice-cooling, to a solution of 532 mg of 4-methoxybenzyl mercaptan dissolved in 10 ml of dry dimethylformamide. The mixture was then stirred at room temperature for 30 minutes, after which 1.05 g of (2S, 4R)-1-(t-butoxycarbonyl)-2-(N,N-dimethylcarbamoyl)-4-methanesulfonyloxypyrrolidine [prepared as described in step (2) above] was added. The reaction mixture was then stirred at room temperature for 30 minutes and then at 40° C. for 6 hours. At the end of this time, it was treated and purified according to the procedure described in Preparation 1-(4), to afford 385 mg of the title compound as an oil. |
Here is a chemical reaction formula: Reactants are:m1_m2:O1CCOCC1;m1_m2:Cl;m4:C([O-])(O)=O.[Na+];m3:C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](C1)SCC1=CC=C(C=C1)OC)C(N(C)C)=O, Reagents are:m5:C(C)(=O)OCC, and Products are 0:CN(C(=O)[C@H]1NC[C@H](C1)SCC1=CC=C(C=C1)OC)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1 ml of a 4N dioxane solution of hydrogen chloride was added, whilst ice-cooling, to a solution of 385 mg of (2S, 4S)-1-(t-butoxycarbonyl)-2-(N,N-dimethylcarbamoyl)-4-(4-methoxybenzylthio)pyrrolidine [prepared as described in step (3) above] dissolved in 1 ml of ethyl acetate, and the mixture was stirred at room temperature for 1.5 hours. At the end of this time, the reaction mixture was poured into a saturated aqueous solution of sodium bicarbonate to make it weakly basic, and it was extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, and the residue was purified by column chromatography through silica gel (eluted with a 1:2 by volume mixture of ethyl acetate and methanol), to afford 163 mg of the title compound as an oil. |
Here is a chemical reaction formula: Reactants are:m3:CN(C(=O)[C@H]1NC[C@H](C1)SCC1=CC=C(C=C1)OC)C;m4:C([O-])(O)=O.[Na+];m1_m2:C([O-])(O)=O.[Na+];m1_m2:CI, Reagents are:m5:CN(C=O)C, and Products are 0:CN(C(=O)[C@H]1N(C[C@H](C1)SCC1=CC=C(C=C1)OC)C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 84 mg of sodium bicarbonate and 41 μl of methyl iodide were added, whilst ice-cooling, to a solution of 163 mg of (2S, 4S)-2-(N,N-dimethylcarbamoyl)-4-(4-methoxybenzylthio)pyrrolidine [prepared as described in step (4) above] dissolved in 1.5 ml of dry dimethylformamide, and the mixture was stirred at room temperature for 4 hours. At the end of this time, the reaction mixture was poured into a saturated aqueous solution of sodium bicarbonate and extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, and the residue was purified by chromatography using a Lobar column (Merck, LiChroprep Si60, size A). 45 mg of the title compound were obtained, as an oil, from the fractions eluted with a 3:1 by volume mixture of ethyl acetate and methanol. |
Here is a chemical reaction formula: Reactants are:m3:C(C)(C)(C)OC(=O)N1[C@H](C(=O)OC)CC(C1)O;m2:C(C)N(CC)CC;m1:CS(=O)(=O)Cl;m4:[Cl-].[Na+], Reagents are:m5:O1CCCC1, and Products are 0:C(C)(C)(C)OC(=O)N1[C@@H](C[C@H](C1)OS(=O)(=O)C)C(=O)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 2.02 ml of methanesulfonyl chloride, followed by 3.65 ml of triethylamine were added, whilst ice-cooling, to a solution of 6.1 g of methyl 1-(t-butoxycarbonyl)-4-hydroxyprolinate [prepared as described in step (6) above] dissolved in 120 ml of dry tetrahydrofuran. The mixture was stirred first at 0° to 5° C. for 1 hour and then at room temperature for 1 hour, after which it was poured into an aqueous solution of sodium chloride and extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, to afford 8.13 g of the title compound as an oil. |
Here is a chemical reaction formula: Reactants are:m1:[H-].[Na+];m3_m6:C(C)(C)(C)OC(=O)N1[C@@H](C[C@H](C1)OS(=O)(=O)C)C(=O)OC;m2:COC1=CC=C(CS)C=C1;m4:[Cl-].[Na+], Reagents are:m3_m6:CN(C=O)C;m5:CN(C=O)C, and Products are 0:C(C)(C)(C)OC(=O)N1C(CC(C1)SCC1=CC=C(C=C1)OC)C(=O)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1.11 g of sodium hydride (as a 55% w/w dispersion in mineral oil) was added, whilst ice-cooling, to a solution of 3.51 ml of 4-methoxybenzyl mercaptan dissolved in 60 ml of dry dimethylformamide, and the mixture was stirred at room temperature for 30 minutes. At the end of this time, a solution of 8.13 g of (2S, 4R)-1-(t-butoxycarbonyl)-4-methanesulfonyloxy-2-methoxycarbonylpyrrolidine [prepared as described in step (7) above] in 20 ml of dry dimethylformamide was added dropwise to the mixture, which was then stirred at room temperature for 15 minutes and then at 40° C. for 4 hours. The reaction mixture was then poured into an aqueous solution of sodium chloride and extracted with ethyl acetate. The extract was washed with water, dried and freed from the solvent by distillation under reduced pressure. The residue was purified by column chromatography through silica gel (eluted with a 15:1 by volume mixture of benzene and ethyl acetate), to afford 6.89 g of the title compound as an oil. |
Here is a chemical reaction formula: Reactants are:m3:C([O-])(O)=O.[Na+];m5_m1:Cl;m2:C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](C1)SCC1=CC=C(C=C1)OC)C(=O)OC, Reagents are:m5_m1:C(C)(=O)OCC;m4:C(C)(=O)OCC, and Products are 0:COC1=CC=C(CS[C@H]2C[C@H](NC2)C(=O)OC)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 27.3 ml of a 4N ethyl acetate solution of hydrogen chloride were added, whilst ice-cooling, to a solution of 5.22 g of (2S, 4S)-1-(t-butoxycarbonyl)-4-(4-methoxybenzylthio)-2-methoxycarbonylpyrrolidine [prepared as described in step (8) above] dissolved in 14 ml of ethyl acetate, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was then poured into a saturated aqueous solution of sodium bicarbonate and extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, to give 3.3 g of the title compound as an oil. |
Here is a chemical reaction formula: Reactants are:m1_m2:C([O-])(O)=O.[Na+];m1_m2:CI;m3:COC1=CC=C(CS[C@H]2C[C@H](NC2)C(=O)OC)C=C1;m4:C([O-])(O)=O.[Na+], Reagents are:m5:CN(C=O)C, and Products are 0:COC1=CC=C(CS[C@H]2C[C@H](N(C2)C)C(=O)OC)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1.18 g of sodium bicarbonate and 0.876 ml of methyl iodide were added, whilst ice-cooling, to a solution of 3.3 g of (2S, 4S)-4-(4-methoxybenzylthio)-2-methoxycarbonylpyrrolidine [prepared as described in step (9) above] dissolved in 30 ml of dry dimethylformamide, and the mixture was stirred at room temperature for 5 hours. At the end of this time, the reaction mixture was poured into a saturated aqueous solution of sodium bicarbonate and extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography over silica gel (eluted with a 1:2 by volume mixture of ethyl acetate and benzene), to afford 968 mg of the title compound as an oil. |
Here is a chemical reaction formula: Reactants are:m1:FS(=O)(=O)OC;m2:CN(C(=O)[C@H]1N(C[C@H](C1)SCC1=CC=C(C=C1)OC)C)C, Reagents are:m3:C(Cl)Cl, and Products are 0:FS(=O)(=O)[O-].CN(C(=O)[C@H]1[N+](C[C@H](C1)SCC1=CC=C(C=C1)OC)(C)C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 139 μl of methyl fluorosulfonate were added, whilst ice-cooling, to a solution of 190 mg of (2S, 4S)-2-(N,N-dimethylcarbamoyl)-4-(4-methoxybenzylthio)-1-methylpyrrolidine [prepared as described in step (5) or (11) above] dissolved in 3.8 ml of methylene chloride, and the mixture was stirred at room temperature for 2 hours. At the end of this time, the solvent was distilled off under reduced pressure. The residue was repeatedly washed by decantation with hexane and dried under reduced pressure, to give 356 mg of the title compound as an oil. |
Here is a chemical reaction formula: Reactants are:m3:C(C)(C)(C)OC(=O)N1C[C@@H](CC1)O;m1_m2:C(C)N(CC)CC;m1_m2:CS(=O)(=O)Cl;m4:[Cl-].[Na+], Reagents are:m5:O1CCCC1, and Products are 0:C(C)(C)(C)OC(=O)N1C[C@@H](CC1)OS(=O)(=O)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 16.91 ml of triethylamine and 9.36 ml of methanesulfonyl chloride were added, in that order, whilst ice-cooling, to a solution of 25 g of (3R)-1-t-butoxycarbonyl-3-hydroxypyrrolidine dissolved in 250 ml of dry tetrahydrofuran, and the mixture was stirred at 0° to 5° C. for 30 minutes and then at 15° C. for 30 minutes. At the end of this time, the mixture was poured into an aqueous solution of sodium chloride and extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, to give 3.10 g of the title compound as a colorless oil. |
Here is a chemical reaction formula: Reactants are:m2:COC1=CC=C(CS)C=C1;m1:[H-].[Na+];m4:[Cl-].[Na+];m3_m6:C(C)(C)(C)OC(=O)N1C[C@@H](CC1)OS(=O)(=O)C, Reagents are:m5:CN(C=O)C;m3_m6:CN(C=O)C, and Products are 0:C(C)(C)(C)OC(=O)N1C[C@H](CC1)SCC1=CC=C(C=C1)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 5.32 g of sodium hydride (as a 55% w/w dispersion in mineral oil) were added, whilst ice-cooling, to a solution of 16.86 ml of 4-methoxybenzyl mercaptan dissolved in 200 ml of dry dimethylformamide, and the mixture was then stirred at room temperature for 30 minutes. At the end of this time, a solution of 31.00 g of (3R)-1-t-butoxycarbonyl-3-methanesulfonyloxypyrrolidine [prepared as described in step (1) above] in 50 ml of dry dimethylformamide was added to the reaction mixture. The mixture was then stirred for 30 minutes whilst ice-cooling, after which it was allowed to stand overnight at room temperature. It was then poured into an aqueous solution of sodium chloride and extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by column chromatography through silica gel (eluted with a 5:1 by volume mixture of hexane and ethyl acetate), to afford 28.00 g of the title compound a pale-brown oil. |
Here is a chemical reaction formula: Reactants are:m5_m1:Cl;m2:C(C)(C)(C)OC(=O)N1C[C@@H](CC1)SCC1=CC=C(C=C1)OC, Reagents are:m3:C(C)(=O)OCC;m5_m1:C(C)(=O)OCC;m4:C(C)(C)OC(C)C, and Products are 0:Cl.COC1=CC=C(CS[C@@H]2CNCC2)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 106 ml of a 4N ethyl acetate solution of hydrogen chloride were added, whilst ice-cooling, to a solution of 27.50 g of (3R)-1-t-butoxycarbonyl-3-(4-methoxybenzylthio)pyrrolidine [prepared as described in step (2) above] dissolved in 100 ml of ethyl acetate, and the mixture was stirred at 0° to 5° C. for 30 minutes and then at 25° C. for 2 hours. At the end of this time, the mixture was diluted with 200 ml of diisopropyl ether, and the crystals which precipitated were collected by filtration, to give 20.84 g of the title compound as colorless crystals, melting at 125°-126° C. |
Here is a chemical reaction formula: Reactants are:m2:COC1=CC=C(CS[C@@H]2CN(CC2)C)C=C1;m1:FS(=O)(=O)OC, Reagents are:m3:C(Cl)Cl, and Products are 0:FS(=O)(=O)[O-].C[N+]1(C[C@H](CC1)SCC1=CC=C(C=C1)OC)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 118 μl of methyl fluorosulfonate were added, whilst ice-cooling, to a solution of 340 mg of (3S)-3-(4-methoxybenzylthio)-1-methylpyrrolidine [prepared as described in step (4) above] dissolved in 20 ml of dry methylene chloride. The mixture was then stirred at the same temperature for 30 minutes and then at room temperature for 3.5 hours. At the end of this time, the solvent was removed by distillation under reduced pressure, and the residue was repeatedly washed by decantation with diethyl ether and dried under reduced pressure to afford 500 mg of the title compound as a colorless powder. |
Here is a chemical reaction formula: Reactants are:m3:OC1CCN(CC1)C;m4:[Cl-].[Na+];m1_m2:C(C)N(CC)CC;m1_m2:CS(=O)(=O)Cl, Reagents are:m5:O1CCCC1, and Products are 0:CS(=O)(=O)OC1CCN(CC1)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 13.3 ml of triethylamine and subsequently 7.4 ml of methanesulfonyl chloride were added, whilst ice-cooling, to a solution of 10 g of 4-hydroxy-1-methylpiperidine dissolved in 100 ml of dry tetrahydrofuran. The mixture was then stirred at 0° to 5° C. for 2 hours and then at room temperature for 1.5 hours, after which it was poured into an aqueous solution of sodium chloride and extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was then distilled off under reduced pressure, to afford 12.74 g of the title compound as an oil. |
Here is a chemical reaction formula: Reactants are:m3_m6:CS(=O)(=O)OC1CCN(CC1)C;m1_m5:COC1=CC=C(CS)C=C1;m2:[H-].[Na+];m4:[Cl-].[Na+], Reagents are:m3_m6:CN(C=O)C;m1_m5:CN(C=O)C, and Products are 0:COC1=CC=C(CSC2CCN(CC2)C)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 10.9 ml of 4-methoxybenzyl mercaptan were dissolved in 55 ml of dry dimethylformamide, and 3.4 g of sodium hydride (as a 55% w/w suspension in mineral oil) were added to the solution, whilst ice-cooling. The mixture was then stirred at room temperature for 30 minutes. At the end of this time, a solution of 12.6 g of 4-methanesulfonyloxy-1-methylpiperidine in 63 ml of dry dimethylformamide was added to the mixture, which was then allowed to stand overnight at room temperature. The reaction mixture was then poured into an aqueous solution of sodium chloride and extracted with ethyl acetate. The extract as washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, and the residue was purified by column chromatography through silica gel (eluted with a 1:4 by volume mixture of ethyl acetate and methanol) to afford 9.01 g of the title compound as an oil. |
Here is a chemical reaction formula: Reactants are:m1_m2:FS(=O)(=O)OC;m1_m2:CN(C(=O)[C@H]1N(C[C@H](C1)SCC1=CC=C(C=C1)OC)CC)C, Reagents are:m3:C(Cl)Cl, and Products are 0:FS(=O)(=O)[O-].CN(C(=O)[C@H]1[N+](C[C@H](C1)SCC1=CC=C(C=C1)OC)(C)CC)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 128 μl of methyl fluorosulfonate were added to a solution of 438 mg of (2S, 4S)-2-(N,N-dimethylcarbamoyl)-1-ethyl-4-(4-methoxybenzylthio)pyrrolidine dissolved in 10 ml of methylene chloride, and the mixture was stirred at room temperature for 2 hours. At the end of this time, the solvent was removed by distillation under reduced pressure, and the residue was washed repeatedly by decantation with diethyl ether and dried under reduced pressure to afford the title compound as an oil. |
Here is a chemical reaction formula: Reactants are:m4:C([O-])(O)=O.[Na+];m1_m2_m3_m5:C(C)I;m1_m2_m3_m5:C([O-])(O)=O.[Na+];m1_m2_m3_m5:C(N)(=O)[C@H]1NC[C@H](C1)SCC1=CC=C(C=C1)OC, Reagents are:m1_m2_m3_m5:CN(C=O)C, and Products are 0:C(N)(=O)[C@H]1N(C[C@H](C1)SCC1=CC=C(C=C1)OC)CC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 0.362 ml of ethyl iodide and 315 mg of sodium bicarbonate to a solution of 1000 mg of (2S, 4S)-2-carbamoyl-4-(4-methoxybenzylthio)pyrrolidine dissolved in 10 ml of dry dimethylformamide were added, whilst ice-cooling, and the mixture was stirred at room temperature for 5.5 hours. At the end of this time, the reaction mixture was poured into a saturated aqueous solution of sodium bicarbonate and extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent was removed by distillation under reduced pressure. The residue was subjected to column chromatography through silica gel (Katayama Chemicals Co., Silica Gel 60K070) and 560 mg of the title compound were obtained as crystals, melting at 124°-125° C., from the fractions eluted with ethyl acetate. |
Here is a chemical reaction formula: Reactants are:m1:FS(=O)(=O)OC;m2:C(N)(=O)[C@H]1N(C[C@H](C1)SCC1=CC=C(C=C1)OC)CC, Reagents are:m3:C(Cl)Cl, and Products are 0:FS(=O)(=O)[O-].C(N)(=O)[C@H]1[N+](C[C@H](C1)SCC1=CC=C(C=C1)OC)(C)CC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 0.43 ml of methyl fluorosulfonate was added, whilst ice-cooling, to a solution of 1.44 g of (2S, 4S)-2-carbamoyl-4-(4-methoxybenzylthio)-1-ethylpyrrolidine dissolved in 30 ml of dry methylene chloride and the mixture was stirred at room temperature for 2 hours. At the end of this time, the solvent was removed by distillation under reduced pressure, and the residue was washed repeatedly by decantation with diethyl ether and dried under reduced pressure to afford 2.0 g of the title compound as an oil. |
Here is a chemical reaction formula: Reactants are:m4:[Cl-].[Na+];m7_m1_m5_m2:ClC(=O)OCC;m7_m1_m5_m2:C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](C1)O)C(=O)O;m3:C(C)N, Reagents are:m7_m1_m5_m2:O1CCCC1;m7_m1_m5_m2:C(C)N(CC)CC;m6:O1CCCC1, and Products are 0:C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](C1)O)C(NCC)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 15.25 ml of triethylamine and subsequently a solution of 10.48 ml of ethyl chloroformate in 50 ml of dry tetrahydrofuran were added at -25° C. to a solution of 23.13 g of (2S, 4S)-1-t-butoxycarbonyl-4-hydroxy-2-pyrrolidinecarboxylic acid dissolved in 350 ml of dry tetrahydrofuran, and the mixture was stirred at the same temperature for 30 minutes. At the end of this time, a 70% by volume aqueous ethylamine solution was added at -22° C., the reaction temperature was allowed to rise gradually and the reaction finished when the temperature reached 10° C. The reaction mixture was then mixed with a small amount of an aqueous solution of sodium chloride, after which it was extracted thrice with ethyl acetate. The combined extracts were washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, to afford 23.60 g of the title compound as a colorless oil. |
Here is a chemical reaction formula: Reactants are:m1_m2:C(C)N(CC)CC;m1_m2:CS(=O)(=O)Cl;m3:C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](C1)O)C(NCC)=O;m4:[Cl-].[Na+], Reagents are:m5:O1CCCC1, and Products are 0:C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](C1)OS(=O)(=O)C)C(NCC)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 13.81 ml of triethylamine and subsequently 7.65 ml of methanesulfonyl chloride were added, whilst ice-cooling, to a solution of 23.20 g of (2S, 4S)-1-t-butoxycarbonyl-2-ethylcarbamoyl-4-hydroxypyrrolidine dissolved in 250 ml of dry tetrahydrofuran, and then the mixture was stirred at 0° to 5° C. for 30 minutes. The reaction mixture was then poured into an aqueous solution of sodium chloride and extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, to afford 26.54 g of the title compound as colorless crystals, melting at 138°-140° C. |
Here is a chemical reaction formula: Reactants are:m2:COC1=CC=C(CS)C=C1;m4:[Cl-].[Na+];m1:[H-].[Na+];m3_m6:C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](C1)OS(=O)(=O)C)C(NCC)=O, Reagents are:m5:CN(C=O)C;m3_m6:CN(C=O)C, and Products are 0:C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](C1)SCC1=CC=C(C=C1)OC)C(NCC)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 3.57 g of sodium hydride (as a 55% w/w suspension in mineral oil) was added, whilst ice-cooling, to a solution of 11.31 ml of 4-methoxybenzyl mercaptan dissolved in 150 ml of dry dimethylformamide and the mixture was stirred at 0° to 5° C. for 30 minutes. A solution of 26.00 g of (2S, 4S)-1-t-butoxycarbonyl-2-ethylcarbamoyl-4-methanesulfonyloxypyrrolidine in 100 ml of dry dimethylformamide was then added to the resulting mixture, and the whole was stirred at room temperature for 2 hours. At the end of this time, the reaction mixture was poured into an aqueous solution of sodium chloride and extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. At the end of this time, the solvent was removed by distillation under reduced pressure, and the residue was purified by column chromatography through silica gel using a 1:1 by volume mixture of hexane and ethyl acetate as an eluent, to afford 17.00 g of the title compound as colorless crystals, melting at 92°-94° C. |
Here is a chemical reaction formula: Reactants are:m5_m1_m2:Cl;m5_m1_m2:C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](C1)SCC1=CC=C(C=C1)OC)C(NCC)=O;m3:C([O-])(O)=O.[Na+], Reagents are:m5_m1_m2:C(C)(=O)OCC;m4:C(C)(=O)OCC, and Products are 0:C(C)NC(=O)[C@H]1NC[C@H](C1)SCC1=CC=C(C=C1)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 41.19 ml of a 4N ethyl acetate solution of hydrogen chloride were added to a solution of 13.00 g of (2S, 4S)-1-t-butoxycarbonyl-2-ethylcarbamoyl-4-(4-methoxybenzylthio)pyrrolidine dissolved in 100 ml of ethyl acetate, and the mixture was stirred at room temperature for 3 hours. At the end of this time, the reaction mixture was poured into a saturated aqueous solution of sodium bicarbonate and extracted with ethyl acetate. The aqueous layer was saturated with ammonium chloride and extracted with tetrahydrofuran. The combined extracts were washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent was removed by distillation under reduced pressure. The residue was subjected to column chromatography through silica gel (eluted with a 87:13 by volume mixture of ethyl acetate and methanol) to afford 8.00 g of the title compound as pale brown crystals, melting at 67°-68° C. |
Here is a chemical reaction formula: Reactants are:m1_m2:C(C)I;m1_m2:C([O-])(O)=O.[Na+];m3:C(C)NC(=O)[C@H]1NC[C@H](C1)SCC1=CC=C(C=C1)OC;m4:[Cl-].[Na+], Reagents are:m5:CN(C=O)C, and Products are 0:C(C)NC(=O)[C@H]1N(C[C@H](C1)SCC1=CC=C(C=C1)OC)CC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 301 μl of ethyl iodide and 314 mg of sodium bicarbonate were added, whilst ice-cooling, to a solution of 1.00 g of (2S, 4S)-2-ethylcarbamoyl-4-(4-methoxybenzylthio)pyrrolidine dissolved in 8 ml of dry dimethylformamide, and the mixture was stirred at room temperature for 5 hours. At the end of this time, the reaction mixture was poured into an aqueous solution of sodium chloride and extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, after which the solvent was removed by distillation under reduced pressure. The residue was subjected to column chromatography through silica gel (eluted with ethyl acetate) to afford 982 mg of the title compound as colorless crystals, melting at 60°-61° C. |
Here is a chemical reaction formula: Reactants are:m2:C(C)NC(=O)[C@H]1N(C[C@H](C1)SCC1=CC=C(C=C1)OC)CC;m1:FS(=O)(=O)OC, Reagents are:m3:C(Cl)Cl, and Products are 0:FS(=O)(=O)[O-].C(C)NC(=O)[C@H]1[N+](C[C@H](C1)SCC1=CC=C(C=C1)OC)(C)CC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 233 μl of methyl fluorosulfonate were added, whilst ice-cooling, to a solution of 910 mg of (2S, 4S)-2-ethylcarbamoyl-1-ethyl-4-(4-methoxybenzylthio)pyrrolidine dissolved in 35 ml of dry methylene chloride, and the mixture was stirred at room temperature for 3.5 hours. At the end of this time, the solvent was removed by distillation under reduced pressure, and the residue was washed by decantation with diethyl ether and dried under reduced pressure, to afford 1.20 g of the title compound as a pale brown oil. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:C(C)I;m1_m2_m3:C([O-])(O)=O.[Na+];m1_m2_m3:COC1=CC=C(CS[C@H]2C[C@H](NC2)C(NC)=O)C=C1;m4:[Cl-].[Na+], Reagents are:m5:CN(C=O)C, and Products are 0:C(C)N1[C@@H](C[C@@H](C1)SCC1=CC=C(C=C1)OC)C(NC)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 0.71 ml of ethyl iodide and 742 mg of sodium bicarbonate were added to a solution of 2.25 g of (2S, 4S)-4-(4-methoxybenzylthio)-2-methylcarbamoylpyrrolidine dissolved in 20 ml of dry dimethylformamide, and the mixture was stirred at 0° to 5° C. for 1 hour and then at room temperature for 5 hours. At the end of this time, the reaction mixture was poured into an aqueous solution of sodium chloride and extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, after which the solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography (eluted with ethyl acetate), to afford 1.87 g of the title compound as colorless crystals, melting at 68°-70° C. |
Here is a chemical reaction formula: Reactants are:m1:FS(=O)(=O)OC;m2:C(C)N1[C@@H](C[C@@H](C1)SCC1=CC=C(C=C1)OC)C(NC)=O, Reagents are:m3:C(Cl)Cl, and Products are 0:FS(=O)(=O)[O-].C(C)[N+]1([C@@H](C[C@@H](C1)SCC1=CC=C(C=C1)OC)C(NC)=O)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 187 μl of methyl fluorosulfonate were added, whilst ice-cooling, to a solution of 700 mg of (2S, 4S)-1-ethyl-4-(4-methoxybenzylthio)-2-methylcarbamoylpyrrolidine dissolved in 30 ml of dry methylene chloride, and the mixture was stirred at room temperature for 4 hours. At the end of this time, the solvent was removed by distillation under reduced pressure, and the residue was washed repeatedly by decantation with diethyl ether and dried under reduced pressure to afford 950 mg of the title compound as a colorless oil. |
Here is a chemical reaction formula: Reactants are:m1:C(C)(C)(C)OC(=O)N1[C@@H](CCC1)COS(=O)(=O)C;m2_m3_m4_m5:C(C)(C)(C)OC(=O)N1[C@@H](CCC1)CO;m2_m3_m4_m5:COC1=CC=C(CS)C=C1;m2_m3_m4_m5:[H-].[Na+], Reagents are:m2_m3_m4_m5:CN(C=O)C, and Products are 0:C(C)(C)(C)OC(=O)N1[C@@H](CCC1)CSCC1=CC=C(C=C1)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The procedure described in Preparation 5-(2) was repeated, but using 12.16 g of (2S)-1-t-butoxycarbonyl-2-methanesulfonyloxymethylpyrrolidine [prepared by the methanesulfonylation of (2S)-1-t-butoxycarbonyl-2-hydroxymethylpyrrolidine], 7.3 ml of 4-methoxybenzyl mercaptan and 2.3 g of sodium hydride (as a 55% w/w suspension in mineral oil) in 100 ml of dry dimethylformamide, to afford 13.93 g of the title compound as an oil. |
Here is a chemical reaction formula: Reactants are:m2:C=O;m3:C(#N)[BH3-].[Na+];m1:COC1=CC=C(CSC[C@H]2NCCC2)C=C1, Reagents are:m4:C(C)#N, and Products are 0:COC1=CC=C(CSC[C@H]2N(CCC2)C)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The procedure described in Preparation 5-(4) was repeated, but using 2 g of (2S)-2-(4-methoxybenzylthiomethyl)pyrrolidine, 35% formalin and 848 mg of sodium cyanoborohydride in the presence of 44 ml of acetonitrile, to afford 883 mg of the title compound as an oil. |
Here is a chemical reaction formula: Reactants are:m1:COC1=CC=C(CSC[C@H]2N(CCC2)C)C=C1;m2:FS(=O)(=O)OC, Reagents are:m3:C(Cl)Cl, and Products are 0:FS(=O)(=O)[O-].C[N+]1([C@@H](CCC1)CSCC1=CC=C(C=C1)OC)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The procedure described in Preparation 5-(5) was repeated, but using 740 mg of (2S)-2-(4-methoxybenzylthiomethyl)-1-methylpyrrolidine and 243 μl of methyl fluorosulfonate in the presence of 22 ml of methylene chloride, to afford 1.0 g of the title compound as crystals, melting at 150°-153° C. |
Here is a chemical reaction formula: Reactants are:m1_m2:ICCO;m1_m2:C([O-])(O)=O.[Na+];m4:C([O-])(O)=O.[Na+];m3:C(N)(=O)[C@H]1NC[C@H](C1)SCC1=CC=C(C=C1)OC, Reagents are:m5:CN(C=O)C, and Products are 0:C(N)(=O)[C@H]1N(C[C@H](C1)SCC1=CC=C(C=C1)OC)CCO, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 0.175 ml of 2-iodoethanol and 0.16 g of sodium bicarbonate were added, whilst ice-cooling, to a solution of 0.5 g of (2S, 4S)-2-carbamoyl-4-(4-methoxybenzylthio)pyrrolidine [prepared as described in Preparation 1-(5)] dissolved in 5 ml of dry dimethylformamide, and the mixture was stirred at the same temperature for 1 hour, at room temperature for 2.5 hours, and at 40° C. for 19 hours. The reaction mixture was then poured into a saturated aqueous solution of sodium bicarbonate and extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, and the residue was subject to column chromatography through silica gel (Wako Pure Chemicals, Ltd.; wako gel C-100). 0.465 g of the title compound was obtained as crystals from the fractions eluted with a 95:5 by volume mixture of ethyl acetate and methanol. |
Here is a chemical reaction formula: Reactants are:m1_m2:FS(=O)(=O)OC;m1_m2:C(N)(=O)[C@H]1N(C[C@H](C1)SCC1=CC=C(C=C1)OC)CCO, Reagents are:m3:C(Cl)Cl, and Products are 0:FS(=O)(=O)[O-].C(N)(=O)[C@H]1[N+](C[C@H](C1)SCC1=CC=C(C=C1)OC)(C)CCO, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 0.108 ml of methyl fluorosulfonate was added dropwise at room temperature to a solution of 0.38 of (2S, 4S)-2-carbamoyl-1-(2-hydroxyethyl)-4-(4-methoxybenzylthio)pyrrolidine dissolved in 7.5 ml of dry methylene chloride, and the mixture was stirred at the same temperature for 2 hours. At the end of this time, the solvent was removed by distillation under reduced pressure, and the residue was washed by decantation with diethyl ether and dried under reduced pressure, to afford 0.396 g of the title compound as an oil. |
Here is a chemical reaction formula: Reactants are:m2_m3_m4:N12CC(C(CC1)CC2)O;m2_m3_m4:COC1=CC=C(CS)C=C1;m2_m3_m4:[H-].[Na+];m1:CS(=O)(=O)OC1CN2CCC1CC2, Reagents are:, and Products are 0:COC1=CC=C(CSC2CN3CCC2CC3)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The procedure described in Preparation 6-(2) was repeated, but using 3.7 g of 3-methanesulfonyloxyquinuclidine (prepared by the methanesulfonylation of 3-quinuclidinol), 3.0 ml of 4-methoxybenzyl mercaptan and 0.942 g of sodium hydride (as a 55% w/w suspension in mineral oil), to afford 1.74 g of the title compound as an oil. |
Here is a chemical reaction formula: Reactants are:m2:FS(=O)(=O)OC;m1:COC1=CC=C(CSC2CN3CCC2CC3)C=C1, Reagents are:m3:C(Cl)Cl, and Products are 0:FS(=O)(=O)[O-].COC1=CC=C(CSC2C[N+]3(CCC2CC3)C)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The procedure described in Preparation 6-(3) was repeated, but using 756 mg of 3-(4-methoxybenzylthio)-quinuclidine and 271 μl of methyl fluorosulfonate in the presence of 5 ml of methylene chloride, to afford 1.078 g of the title compound as an oil. |
Here is a chemical reaction formula: Reactants are:m4:[Cl-].[Na+];m1_m2:ICCO;m1_m2:C([O-])(O)=O.[Na+];m3:COC1=CC=C(CS[C@H]2C[C@H](NC2)C(NC)=O)C=C1, Reagents are:m5:CN(C=O)C, and Products are 0:OCCN1[C@@H](C[C@@H](C1)SCC1=CC=C(C=C1)OC)C(NC)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 934 μl of 2-iodoethanol and 1.01 g of sodium bicarbonate were added, whilst ice-cooling, to a solution of 2.80 g of (2S, 4S)-4-(4-methoxybenzylthio)-2-methylcarbamoylpyrrolidine dissolved in 18 ml of dry dimethylformamide, and the mixture was stirred at 40° C. for 24 hours. At the end of this time, the reaction mixture was poured into an aqueous solution of sodium chloride and extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, and the residue was purified by column chromatography through silica gel (eluted with a 15:1 by volume mixture of ethyl acetate and methanol), to afford 2.22 g of the title compound as colorless crystals, melting at 88°-89.5° C. |
Here is a chemical reaction formula: Reactants are:m1_m2:C(C)N(CC)CC;m1_m2:CS(=O)(=O)Cl;m3:OCCN1[C@@H](C[C@@H](C1)SCC1=CC=C(C=C1)OC)C(NC)=O, Reagents are:m4:O1CCCC1, and Products are 0:CS(=O)(=O)OCCN1[C@@H](C[C@@H](C1)SCC1=CC=C(C=C1)OC)C(NC)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1.06 ml of triethylamine and subsequently 584 μl of methanesulfonyl chloride were added, whilst ice-cooling, to a solution of 2.13 g of (2S, 4S)-1-(2-hydroxyethyl)-4-(4-methoxybenzylthio)-2-methylcarbamoylpyrrolidine dissolved in 45 ml of dry tetrahydrofuran, and the mixture was stirred at 0° to 5° C. for 30 minutes. At the end of this time, the crystals which precipitated were collected by filtration and washed with tetrahydrofuran. The filtrate and washings were combined and dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure, to afford 2.50 g of the title compound as an oil. |
Here is a chemical reaction formula: Reactants are:m1:[H-].[Na+];m2:CS(=O)(=O)OCCN1[C@@H](C[C@@H](C1)SCC1=CC=C(C=C1)OC)C(NC)=O;m3:[Cl-].[Na+], Reagents are:m4:CN(C=O)C, and Products are 0:COC1=CC=C(CS[C@H]2C[C@H]3C(N(CCN3C2)C)=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 347 mg of sodium hydride (as a 55% w/w suspension in mineral oil) was added, whilst ice-cooling, to a solution of 2.64 g of (2S, 4S)-1-(2-methanesulfonyloxyethyl)-4-(4-methoxybenzylthio)-2-methylcarbamoylpyrrolidine dissolved in 30 ml of dry dimethylformamide, and the mixture was stirred at 0° to 5° C. for 30 minutes and then at 30° C. for 2 hours. The reaction mixture was then poured into an aqueous solution of sodium chloride and extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and freed from the solvent by distillation under reduced pressure. The residue was purified by column chromatography through silica gel (eluted with a 5:1 by volume mixture of acetonitrile and methanol), to afford 1.75 g of the title compound as an oil. |
Here is a chemical reaction formula: Reactants are:m1:FS(=O)(=O)OC;m2:COC1=CC=C(CS[C@H]2C[C@H]3C(N(CCN3C2)C)=O)C=C1, Reagents are:m3:C(Cl)Cl;m4:C(C)OCC, and Products are 0:FS(=O)(=O)[O-].C[N+]12CCN(C([C@@H]2C[C@@H](C1)SCC1=CC=C(C=C1)OC)=O)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 461 μl of methyl fluorosulfonate was added, whilst ice-cooling, to a solution of 1.71 g of (6S, 8S)-8-(4-methoxybenzylthio)-4-methyl-5-oxo-1,4-diazabicyclo-[4.3.0]nonane dissolved in 60 ml of methylene chloride, and the mixture was stirred at room temperature for 2 hours. At the end of this time, the mixture was diluted with diethyl ether, and the resulting crystals were collected by filtration and dried under reduced pressure, to afford 2.09 g of the title compound as colorless crystals, melting at 208°-210° C. |
Here is a chemical reaction formula: Reactants are:m3_m4:COC1=CC=C(CSC2C(NCC2)=O)C=C1;m1_m2:FC(C(=O)O)(F)F;m1_m2:FC(S(=O)(=O)O)(F)F, Reagents are:m3_m4:C1(=CC=CC=C1)OC, and Products are 0:FC(S(=O)(=O)O)(F)F.SC1C(NCC1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 20 ml of trifluoroacetic acid and 0.41 ml of trifluoromethanesulfonic acid were added, whilst ice-cooling, to a solution of 949 mg of 3-(4-methoxybenzylthio)pyrrolidin-2-one in 4 ml of anisole, and then the mixture was stirred at room temperature for 30 minutes. At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure to leave a residue, which was purified by column chromatography through silica gel, eluted with a 10:1 by volume mixture of ethyl acetate and methanol, to give 728 mg of the title compound as an oil. |
Here is a chemical reaction formula: Reactants are:m1_m2_m5:C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1;m1_m2_m5:OC1CC(NC1)=O;m3_m6:N(=NC(=O)OCC)C(=O)OCC;m4:C(C)(=S)O, Reagents are:m1_m2_m5:O1CCCC1;m3_m6:O1CCCC1, and Products are 0:C(C)(=O)SC1CC(NC1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 20-(1) 15.6 g of triphenylphosphine were added to a suspension of 3 g of 4-hydroxy-2-pyrrolidinone in 200 ml of tetrahydrofuran, and then the mixture was stirred at room temperature for 5 minutes, after which it was cooled to -20° C. A solution of 9.3 ml of diethyl azodicarboxylate in 9 ml of tetrahydrofuran was added dropwise, whilst cooling at -12° C. to -20° C., to the previous solution. The mixture was then stirred at 0°-5° C. for 5 minutes, after which it was again cooled to -20° C. 4.2 ml of thioacetic acid were then added dropwise to the mixture, whilst cooling at -18° C. to -20° C. The mixture was then warmed to 0°-5° C. and stirred at that temperature for 2 hours. At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure. The residue was purified first by column chromatography through silica gel, eluted with a 10:1 by volume mixture of ethyl acetate and methanol, and then by column chromatography through silica gel, eluted with a 2:1 by volume mixture of acetonitrile and benzene, to give 2.45 g of 4-acetylthio-2-pyrrolidinone as colorless crystals. |
Here is a chemical reaction formula: Reactants are:m4:C(C)(=O)O;m1_m5_m2:C(C)(C)(C)[Li];m1_m5_m2:ClC1=CC=CC(=N1)OC;m3:CN(C=O)C, Reagents are:m1_m5_m2:C1CCOC1;m6:CCOCC, and Products are 0:ClC1=CC=C(C(=N1)OC)C=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of tert-butyllithium (1.7M in pentane, 48.5 mL, 83.0 mmol) in 150 mL of THF at -78° C. was added 6-chloro-2-methoxypyridine (8.94 mL, 75.0 mmol) over 5 min. The reaction mixture was stirred at -78° C. for 1 h, then dimethylformamide (7.55 mL, 97 mmol) was added and the mixture was stirred at this temperature for 1.5 h. After the addition of glacial acetic acid (8.6 mL, 150 mmol), the reaction mixture was allowed to warm to room temperature over a 30- min period, then diluted with ether (200 mL). The organic phase was washed with saturated aqueous NaHCO3 (100 mL) and brine (100 mL), and was dried over MgSO4. Concentration afforded the crude product as a light yellow solid which was recrystallized from hexanes to give 9.6 g (75%) of 6-chloro-2-methoxy-3-pyridinecarboxaldehyde as a white solid: mp 80°-81° C. (mp 62°-64° C.) (See Dainter, R. S.; Suschitzky, H.; Wakefield, B. J. Tetrahedron Lett. 1984, 25, 5693.). 1H NMR (300 MHz, CDCl3) δ 10.31 (s, 1H), 8.07 (d, 1H, J=9 Hz), 7.03 (d, 1H, J=9 Hz), 4.09 (s, 3H); IR (nujol) 1685, 1580, 1565, 1270, 1140, 1090, 1005, 905, 820, 755 cm-1. |
Here is a chemical reaction formula: Reactants are:m1_m6_m2:CN(CCNC)C;m1_m6_m2:[Li]CCCC;m3:ClC1=CC=C(C(=N1)OC)C=O;m5:II;m4:[Li]CCCC, Reagents are:m1_m6_m2:COCCOC;m7:COCCOC;m8:COCCOC, and Products are 0:ClC1=CC(=C(C(=N1)OC)C=O)I, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of N,N,N'-trimethylethylenediamine (2.46 mL, 19.23 mmol) in 15 mL of 1,2-dimethoxyethane at -23° C. was added n-BuLi (9.22 mL, 19.23 mmol), and the solution was stirred at -23° C. for 20 min. The mixture was transferred using a double-tipped needle to a solution of 6-chloro-2-methoxy-3-pyridinecarboxaldehyde (3.0 g, 17.5 mmol) in 40 mL of 1,2-dimethoxyethane at -23° C. After stirring for 15 min, n-BuLi (12.6 mL, 26.2 mmol) was added and the dark mixture was stirred an additional 2 h at -23° C. The solution was transferred using a double-tipped needle to a solution of iodine (8.04 g, 31.7 mmol) in 40 mL of 1,2-dimethoxyethane at -78° C. After stirring at -78° C. for 30 min, the cooling bath was removed and the reaction mixture was allowed to warm for 20 min, then quenched with water. The mixture was extracted with ether (2×30 mL) and the combined organic layers were washed successively with 30-mL portions of 10% aqueous Na2S2O3, water and brine, and dried over MgSO4. Concentration afforded 4.62 g (89%) of crude product to which was added 50 mL of hexanes. The mixture was stirred and allowed to stand at 5° C. overnight. Filtration gave 2.67 g of 6-Chloro-4-iodo-2-methoxy-3-pyridinecarboxaldehyde as a yellow solid: mp 120°-124° C. Concentration of the hexane washings and purification of the residue by radial preparative thin-layer chromatography (silica gel, 5% ethyl acetate/hexanes) gave an additional 1.41 g of product (mp 120°-124° C.), raising the total yield of the compound to 78%. Recrystallization from hexanes gave an analytical sample as a bright yellow solid: mp 129°-130° C. 1H NMR (300 MHz, CDCl3) δ 10.16 (s, 1H), 7.59 (s, 1H), 4.07 (s, 1H); IR (nujol) 1690, 1350, 1260, 1095, 1010, 900, 840 cm-1. |
Here is a chemical reaction formula: Reactants are:m4:FC(C(=O)O)(F)F;m1_m2_m3:ClC1=CC(=C(C(=N1)OC)C=O)I;m1_m2_m3:C(C)[SiH](CC)CC;m1_m2_m3:CO;m6_m5:C(=O)(O)[O-].[Na+], Reagents are:m6_m5:CCOCC, and Products are 0:ClC1=NC(=C(C(=C1)I)COC)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a mixture of 6-chloro-4-iodo-2-methoxy-3-pyridinecarboxaldehyde (1.07 g, 3.60 mmol), triethylsilane (0.86 mL, 5.40 mmol) and methanol (0.43 mL, 10.6 mmol) at 0° C. was added trifluoroacetic acid (2.2 mL, 28.6 mmol), and the resulting solution was stirred at 25° C. for 14 h. After dilution with ether (30 mL), saturated NaHCO3 was added until the aqueous phase was rendered basic. The aqueous layer was extracted with ether (10 mL), and the combined ether layers were washed with water (10 mL) and brine (10 mL), and dried (Na2SO4). Concentration gave the crude product which was purified by radial PLC (silica gel, 5% ethyl acetate/hexanes) to afford 2-chloro-4-iodo-6-methoxy-5-(methoxymethyl)pyridine as a white solid (1.05 g., 93%): mp 69°-72° C. Recrystallization from hexanes provided an analytical sample: mp 74°-75° C. 1H NMR (300 MHz, CDCl3) δ 7.40 (S, 1H), 4.53 (s, 2H), 3.96 (s, 3H), 3.42 (s, 3H); IR (nujol) 1550, 1300, 1115, 1090, 1020, 940, 905, 830, 720 cm-1. |
Here is a chemical reaction formula: Reactants are:m4:CN(C=O)C;m3:ClC1=NC2=CC=CC=C2C=C1;m1_m5_m2:C(C)(C)NC(C)C;m1_m5_m2:[Li]CCCC, Reagents are:m1_m5_m2:C1CCOC1, and Products are 0:ClC1=NC2=CC=CC=C2C=C1C=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 0.46 mL (3.30 mmol) of diisopropylamine in 8 mL of THF at 0° C. was added 1.53 mL (3.30 mmol) of n-BuLi dropwise. After 20 min the solution was cooled to -78° C. and 2-chloroquinoline (491 mg, 3.0 mmol) was added neat. The mixture was stirred at -78° C. for 30 min, then dimethylformamide (0.39 mL, 5.04 mmol) was added dropwise and the reaction mixture was stirred an additional 30 min at this temperature. After quenching at -78° C. with glacial acetic acid (1 mL), the mixture was warmed to room temperature and diluted with ether (30 mL). The organic phase was washed with saturated NaHCO3 solution (10 mL) and brine (10 mL), and was dried over MgSO4. Concentration afforded 2-chloro-3-quinolinecarboxaldehyde (530 mg, 92%) as a light yellow solid (mp 145°-149° C.), which was used directly in the next step without further purification. Recrystallization from ethyl acetate afforded the pure compound as light yellow needles: mp 149°-150° C. (mp 148°-149° C. reported in Meth-Cohn, O.; Narhe, B.; Tarnowski, B. J. Chem. Soc. Perkin Trans. I 1981, 1520.). 1H NMR (300 MHz, CDCl3) δ 10.57 (s, 1H), 8.77 (s, 1H), 8.08 (d, 1H, J=9 Hz), 8.0 (d, 1H, J=9 Hz), 7.90 (t, 1H, J=9 Hz), 7.67 (t, 1H, J=9 Hz); IR (nujol) 1685, 1575, 1045, 760, 745 cm-1. |
Here is a chemical reaction formula: Reactants are:m1_m3_m2:IC1=NC2=CC=CC=C2C=C1C=O;m1_m3_m2:[BH4-].[Na+], Reagents are:m1_m3_m2:CO, and Products are 0:OCC=1C(=NC2=CC=CC=C2C1)I, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred solution of 2-iodo-3-quinolinecarboxaldehyde (595 mg, 2.10 mmol) in 40 mL of CH3OH at 0° C. was added NaBH4 (86 mg, 2.31 mmol), and the mixture was stirred at 0° C. for 30 min. After concentrating the mixture to approximately one-half of its original volume, water (30 mL) was added and the mixture was allowed to stand at 5° C. overnight. The solids were filtered and the crude product (570 mg, 95%) was recrystallized from methanol to give 3-hydroxymethyl-2-iodoquinoline (505 mg, 84%) as colorless needles: mp 189°-190° C. 1H NMR (300 MHz, CDCl3) δ 8.19 (s, 1H), 7.99 (d, 1H, J=9 Hz), 7.87 (d, 1H, J=9 Hz), 7.68 (m, 1H), 7.58 (t, 1H, J=9 Hz), 5.45 (t, 1H, J=6 Hz), 4.66 (d, 2H, J=6 Hz); IR (nujol) 3350, 1580, 1320, 1125, 1060, 995, 755, 720, cm-1. |
Here is a chemical reaction formula: Reactants are:m4:C(=O)(O)[O-].[Na+];m3:ClN1C(CCC1=O)=O;m2_m5:C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1;m1:OCC=1C(=NC2=CC=CC=C2C1)I, Reagents are:m2_m5:CN(C)C=O, and Products are 0:ClCC=1C(=NC2=CC=CC=C2C1)I, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred mixture of 3-hydroxymethyl-2-iodoquinoline prepared in accordance with Example 10 above (350 mg, 1.23 mmol) and triphenylphosphine (483 mg, 1.84 mmol) in 10 mL of dry DMF at -23° C. was added N-chlorosuccinimide (246 mg, 1.84 mmol), and the mixture was stirred for 1 h at -23° C. After the addition of 40 mL of dilute aqueous NaHCO3, the mixture was extracted with ethyl acetate (20 mL) and then ether (2×15 mL). The combined organic extracts were washed successively with 20-mL portions of dilute NaHCO3, water and brine, and were dried over MgSO4. Concentration and purification of the residue by radial PLC (silica gel, 10% ethyl acetate/hexanes) afforded 312 mg (84%) of 3-chloromethyl-2-iodoquinoline as a white crystalline solid: mp 138°-140° C. Recrystallization from hexanes afforded an analytical sample as colorless needles: mp 139°-140° C. H NMR (300 MHz, CDCl3) δ 8.17 (s, 1H), 8.07 (d, 1H, J=9 Hz), 7.84 (d, 1H, J=9 Hz), 7.75 (t, 1H, J=9 Hz), 7.62 (t, 1H, J=9 Hz), 4.80 (s, 1H); IR (nujol) 1585, 1555, 1260, 1010, 780, 755, 710 cm-1. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:C1=CC=C2C(=C1)C(=C(C(=O)N2)C(=O)O)C(=O)O;m1_m2_m3:P(=O)(Cl)(Cl)Cl, Reagents are:m1_m2_m3:C(Cl)(Cl)Cl, and Products are 0:C1(OC(C=2C(NC=3C=CC=CC3C21)=O)=O)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 2(1H)-Oxo-quinoline-3,4-dicarboxylic acid (2 g), phosphorous oxychloride (4 g) and dry chloroform (30 mL) was heated at reflux for 2 h. The solvent and excess reagents are removed in vacuo and the residue was treated with ice water to afford Furo[3,4-c]quinoline-1,3,4(5H)-trione as a yellow solid. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:C1=CC=C2C(=C1)C(=C(C(=O)N2)C(=O)O)C(=O)O;m1_m2_m3:P(=O)(Cl)(Cl)Cl, Reagents are:m1_m2_m3:CN(C=O)C, and Products are 0:ClC1=NC=2C=CC=CC2C2=C1C(OC2=O)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 2(1H)-Oxo-quinoline-3,4-dicarboxylic acid (2.0 g), phosphorous oxychloride (10 mL) and 8 drops of dimethyl formamide was refluxed with stirring for 20 min. The reaction mixture was concentrated in vacuo and the residue treated with ice water to afford 4-Chloro-furo[3,4-c]quinoline-1,3-dione as a tan solid. |
Here is a chemical reaction formula: Reactants are:m3:[BH4-].[Na+];m2_m4:ClC1=NC=2C=CC=CC2C2=C1C(OC2=O)=O, Reagents are:m2_m4:O1CCCC1, and Products are 0:ClC1=NC=2C=CC=CC2C2=C1C(OC2)=O;0:ClC1=NC=2C=CC=CC2C2=C1COC2=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a well stirred mixture of 4-Chloro-furo[3,4-c]quinoline-1,3-dione (1.9 g) in tetrahydrofuran (10 mL) was added sodium borohydride (400 mg) at 0° C. and stirring was continued for 2 h. The reaction was then quenched with excess 6N HCl and water, and concentrated in vacuo to afford 4-Chloro-furo[3,4-c]quinolin-3(1H)-one as a pink solid along with a small quantity of 4-Chloro-furo[3,4-c]quinolin-1(3H)-one which could be isolated by column chromatography on silica gel. |
Here is a chemical reaction formula: Reactants are:m1_m3_m2_m4:ClC1=NC=2C=CC=CC2C2=C1C(OC2)=O;m1_m3_m2_m4:C(C)(=O)[O-].[Na+], Reagents are:m1_m3_m2_m4:[Pd];m1_m3_m2_m4:C(C)(=O)O, and Products are 0:C1OC(C=2C=NC=3C=CC=CC3C21)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 4-Chloro-furo[3,4-c]quinolin-3(1H)-one (500 mg), 10% Palladium on carbon (100 mg) and sodium acetate (500 mg) in 20 mL of acetic acid was hydrogenated at atmospheric pressure for 2 h. After filtration through celite, the solvent was removed in vacuo, and the residue was taken up in methylene chloride. After filtration the solvent was removed in vacuo to afford Furo[3,4-c]quinolin-3(1H)-one as a solid. |
Here is a chemical reaction formula: Reactants are:m1_m2:C1OC(C=2C=NC=3C=CC=CC3C21)=O;m1_m2:NC1=CC=CC=C1, Reagents are:m3:CCCCCC, and Products are 0:C1(=CC=CC=C1)N1C(C=2C=NC=3C=CC=CC3C2C1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture Furo[3,4-c]quinolin-3(1H)-one (100 mg) and aniline (2 mL) was heated at 180° C. for 5 min. After cooling to room temperature the mixture was slowly diluted with hexane and the resulting product was collected and washed with hexane to afford 2-Phenyl-pyrrolo[3,4-c]quinolin-3(1H)-one. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:C1(=CC=CC=C1)N1C(C=2C=NC=3C=CC=CC3C2C1)=O;m1_m2_m3:ClC1=CC(=CC=C1)C(=O)OO, Reagents are:m1_m2_m3:C(Cl)Cl;m4:C(Cl)Cl, and Products are 0:C1(=CC=CC=C1)N1C(C=2C(NC=3C=CC=CC3C2C1)=O)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 2-Phenyl-pyrrolo[3,4-c]quinolin-3(1H)-one (60 mg), and m-chloroperbenzoic acid (105 mg) in 3 mL of methylene chloride was kept at room temperature for 24 h. The mixture was diluted with methylene chloride and washed with sodium carbonate solution. The organic layer was dried over magnesium sulfate and the solvent was removed in vacuo. The residue was heated at 50° C. for 3 h with 1 mL of acetic anhydride. The reaction was quenched with methanol and made basic with ammonium hydroxide. The reaction mixture was concentrated in vacuo, and the resulting aqueous solution was extracted with ethyl acetate, the organic layer was dried over magnesium sulfate and the solvent was removed in vacuo. The residue was triturated with ether to afford 2-Phenyl-pyrrolo[3,4-c]quinoline-3(1H),4(5H)-dione (Compound 16) as a white solid. |
Here is a chemical reaction formula: Reactants are:m1_m3:S.[Na];m2:[N+](=O)([O-])C1=CC2=C(N=C(S2)S)C=C1, Reagents are:m1_m3:O, and Products are 0:NC1=CC2=C(N=C(S2)S)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 132 Parts of sodium hydrogen sulphide was dissolved in 400 parts of water, and stirred at 20° C. 53 Parts of 6-nitro-2-mercaptobenzothiazole, prepared as described previously herein, was added over 10 minutes; the reaction mixture was then heated to 110° C., and stirred whilst boiling the mixture under reflux conditions. After four hours boiling, the mixture was cooled to between 0° and 5° C. and stirred for one hour. The product, 6-amino-2-mercaptobenzothiazole (30.3 parts), was isolated by filtration, washed sparingly with cold water and dried at 60° C. for 24 hours. |
Here is a chemical reaction formula: Reactants are:m2:C(CCCCCCCC=CCC=CCCCCC)(=O)Cl;m0_m1:C(CCCCCCCC=CCCCCCCCC)(=O)O, Reagents are:, and Products are 0:C(CCCCCCCC=CCCCCCCCC)(=O)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Octadec-9-enoyl chloride (25.5 parts, boiling point 160°-180° C. at 0.12 Torr, 85% yield) was prepared from 28.1 parts of octadec-9-enoic acid using the procedure described in part A of Example 3 for the preparation of octadec-9,12-dienoyl chloride. |
Here is a chemical reaction formula: Reactants are:m1_m4:C1(CC1)C(=O)N1CCC(CC1)C(=O)OCC;m3:B(OC)(OC)OC;m2_m7:[BH4-].[Li+], Reagents are:m1_m4:O1CCCC1;m5:O;m6:O;m2_m7:O1CCCC1, and Products are 0:C1(CC1)C(=O)N1CCC(CC1)CO, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 1-(cyclopropylcarbonyl)-4-carboethoxy piperidine (35 g, 156 mmol) in anhydrous tetrahydrofuran (350 mL) was stirred at ambient temperature under a nitrogen atmosphere. A solution of lithium borohydride in tetrahydrofuran (2M, 78 mL, 156 mmol) was added dropwise. Trimethyl borate (1.77 mL, 15.7 mmol) was added, then the reduction mixture was stirred for about 48 hours. Water was added dropwise with vigorous stirring until the vigorous gas evolution ceased. The mixture was diluted twofold with water and extracted three times with ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered and concentrated in vacuo. Vacuum distillation (bp 165° C., 0.5 mm Hg) gave a clear, colorless liquid (18.2 g): IR (neat): 3410 (br, s), 3094 (w), 3008 (s), 2918 (s), 2858 (s), 1738 (m), 1613 (s), 1448 (s), 1375 (s), 1316 (s); 1H-NMR: 4.7-4.5 (m, 1H), 4.4-4.1 (m, 1H), 3.6-3.4 (m, 2H), 3.2-2.5 (m, 3H), 2.0-1.7 (m, 4H), 1.4-1.1 (m, 1H), 1.0-0.8 (m, 2H), 0.8-0.65 (m, 2H); HRMS: Calcd for C10H17NO2 :183.1259; Found: 183.1250; Anal.: Calcd for C10H17NO2 :C, 65.54, H, 9.35, N, 7.64; Found: C, 65.83, H, 9.43, N, 7.50. |
Here is a chemical reaction formula: Reactants are:m1_m5:C1(CC1)CN1CCC(CC1)CC(=O)C1=CC=C(C=C1)F;m2_m3:C1(=CC=CC=C1)[Mg]Br;m2_m3:CCOCC;m4:[NH4+].[Cl-], Reagents are:m1_m5:O1CCCC1, and Products are 0:C1(CC1)CN1CCC(CC1)CC(O)(C1=CC=CC=C1)C1=CC=C(C=C1)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1-(Cyclopropylmethyl)-4-(2'-(4"-fluorophenyl)-2'-oxoethyl)piperidine (Example 429, 1.0 g, 3.6 mmol) was mixed with dry tetrahydrofuran (10 mL). A solution of phenyl magnesium bromide in ether (3.0M, 3 mL, 9 mmol) was added with stirring. The reaction mixture was stirred for 24 h; poured onto a saturated NH4Cl solution and extracted with ethyl acetate three times. The combined organic layers were dried over magnesium sulfate and filtered. Solvent was removed in vacuo. Trituration with ether-hexanes (1:9) and filtration afforded the title compound, a solid, which was dried in vacuo (0.9 g) mp 115°-116° C.; Anal.: Calcd for C23H28FNO: C, 77.36, H, 7.90, N, 3.92, F, 5.32; Found: C, 77.47, 77.41, H, 8.00, 7.92, N, 3.42, 3.52, F, 5.09. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:C1(CC1)CN1CCC(CC1)COC1=CC=C(C=C1)F;m1_m2_m3:FC1=CC=C(C=C1)[Mg]Br;m1_m2_m3:O1CCCC1, Reagents are:, and Products are 0:C1(CC1)CN1CCC(CC1)CC(O)(C1=CC=C(C=C1)F)C1=CC=C(C=C1)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Following the procedure described for Example 547, the compound of Example 429 (1.0 g, 3.6 mmol) was reacted a solution of 4-fluorophenylmagnesium bromide in tetrahydrofuran (1.0M, 9 mL, 9 mmol) to give the title compound, a solid (1.1 g): mp 119°-121° C.; Anal.: Calcd for C23H27F2NO.0.5H2O: C, 72.60, H, 7.41, N, 3.68, F, 9.99; Found: C, 72.89, 72.84, H, 7.14, 7.21, N, 3.29, 3.24, F, 9.82, 9.67. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:C1(=CC=CC=C1)C(=[N+]=[N-])C1=CC=CC=C1;m1_m2_m3:NC1=C(N=CN1[C@H]1[C@H](OC(C)=O)[C@H](OC(C)=O)[C@H](O1)COC(C)=O)C(=O)O, Reagents are:m1_m2_m3:C(Cl)Cl, and Products are 0:C1(=CC=CC=C1)C(C1=CC=CC=C1)OC(=O)C=1N=CN(C1N)[C@H]1[C@H](OC(C)=O)[C@H](OC(C)=O)[C@H](O1)COC(C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Diphenyldiazomethane (2.0 g, 10.3 mmol) was added to the suspension of 5-amino-1-(2,3,5-tris-O-acetyl-β-D-ribofuranosyl)-1H-imidazole-4-carboxylic acid (3.86 g, 10 mmol) in CH2Cl2 (50 mL). The mixture was stirred at room temperature for 16 h, by which time all the reactants had dissolved. The reaction mixture was poured onto the top of a column of silica gel (100 g, packed in CH2Cl2, collected 100-mL fractions), and the column was washed with 5% EtOAc in CH2Cl2 (300 mL), then the product was eluted with 40% EtOAc in CH2Cl2. Fractions 5 to 10 were combined and concentrated, then pumped under high vacuum overnight to give 5-amino-1-(2,3,5-tris-O-acetyl-β-D-ribofuranosyl)-1H-imidazole-4-carboxylic acid diphenylmethyl ester as a pale yellow foam: 4.86 g (88% yield); IR (CHCl3) 3445, 3345, 1752, and 1678 cm-1 ; HRMS (EI) m/z found 551.1870 [calcd for C28H29N3O9, 551.1904 (M+)]; NMR (CDCl3) δ2.13 (s, 9), 4.32 (d of d, 1,J=12 and 3 Hz), 4.40 (m, 1), 4.47 (d of d, 1,J=12 and 3 Hz), 5.30 (m, 1), 5.45 (t, 1, J=5 Hz), 5.48 (s, 2), 5.67 (d, 1, J=5 Hz), 7.08 (s, 1), 7.25 (m, 3), 7.32 (t, 4,J=7 Hz), UV max (CH3OH) 267 nm (ε12510). |
Here is a chemical reaction formula: Reactants are:m2_m1_m3:C1(=CC=CC=C1)COC(=O)NC=1OC(C2=C(N1)N(CN2)[C@H]2[C@H](O)[C@H](O)[C@H](O2)CO)=O, Reagents are:m2_m1_m3:[Pd];m2_m1_m3:CN(C)C=O, and Products are 0:C1=NC2=C(N1[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)N=C(OC2=O)N, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 10% Palladium on charcoal (172 mg) was added to a solution of 5-[[(phenylmethoxy)carbonyl]amino]-3-(β-D-ribofuranosyl)imidazo[4,5-d][1,3]oxazin-7(1H)-one (172 mg, 0.41 mmol) in DMF (7 mL) and the mixture was stirred at room temperature under a hydrogen atmosphere for 4 h. The mixture was filtered through prewashed Celite and was concentrated under high vacuum. The residue was dissolved in water and filtered through a Millipore Millex-HV filter (0.45 μm). The filtrate was lyophilized to give oxanosine as a white powder: 115 mg, (100%). Crystallization from warm water gave oxanosine (75%) as colorless needles: mp 191°-192° C.; [α]25D -38.7° (c 1, H2O); IR (KBr) 3440-3200, 1802, 1772, and 1550 cm-1 ; MS [(+) FAB]m/z 285 (M+H+); NMR (D2O) δ3.80-3.91 (m, 2), 4.21-4.23 (m, 1), 4.40 (t, 1, J=4.6 Hz), 4.69 (t, 1, J=5.5 Hz), 5.80-5.85 (d, 1, J=5.5 Hz), 7.98 (s, 1); UV max (H2O) 245 nm (ε11760), 287 (8450). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:C1(=CC=CC=C1)C(C1=CC=CC=C1)OC(=O)C=1N=CN(C1NC(=O)NC(=O)OCC1=CC=CC=C1)[C@H]1[C@H](O)[C@H](O)[C@H](O1)CO, Reagents are:m5:[Pd];m1_m2_m3_m4:CN(C)C=O;m1_m2_m3_m4:C1CCOC1;m1_m2_m3_m4:C(C)O, and Products are 0:NC(=O)NC1=C(N=CN1[C@H]1[C@H](O)[C@H](O)[C@H](O1)CO)C(=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 5-[[[[(phenylmethoxy)carbonyl]amino]carbonyl]amino]-1-(β-D-ribofuranosyl)-1H-imidazole-4-carboxylic acid diphenylmethyl ester (1.76 g, 2.9 mmol) was dissolved in the mixture of DMF (50 mL), THF (20 mL) and ethanol (30 mL) and mixed with 10% palladium on charcoal. The mixture was hydrogenated at 50 psig pressure for 2 h. The catalyst was removed by filtration through Celite, and washed extensively with DMF and ethanol. Combined washing and filtrate was concentrated under reduced pressure to dryness. Residue was dissolved in 30% aqueous ethanol and filtered through a C18-Sep-Pak to remove the last traces of catalyst. This eluate was concentrated to dryness and partitioned between water (100 mL) and ether (2×100 mL). The aqueous layer was concentrated to dryness, redissolved in water and evaporated again and pumped under high vacuum to give 5-[[(amino)carbonyl]amino]-1-(β-D-ribofuranosyl)-1H-imidazole-4-carboxylic acid as a colorless glass: yield 0.64 g (73%); IR (KBr) 3340, 1692 cm -1 ; NMR (Me2SO-d6) δ3.72-3.53 (m, 2), 3.84 (d, 1, J=4.3 Hz), 4.05 (s, 1), 4.14 (s, 1), 5.05 (s, 1), 5.11 (s, 1), 5.34 (s, 1), 5.50 (d, 1, J=4.3 Hz), 6.28 (s, 2), 7.92 (s, 1), 8.07 (s, 1); UV max (H2O) 215 nm (ε5800). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:Cl.CN(CCCN=C=NCC)C;m1_m2_m3_m4:NC(=O)NC=1N(C=C(N1)C(=O)O)[C@H]1[C@H](O)[C@H](O)[C@H](O1)CO, Reagents are:m1_m2_m3_m4:O;m1_m2_m3_m4:CO, and Products are 0:C1=NC2=C(N1[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)N=C(OC2=O)N, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (78 mg, 0.41 mmol) was added to a solution of 5-[[(amino)carbonyl]amino-1-(β-D-ribofuranosyl)-1H-imidazole-4-carboxylic acid (19 mg, 0.063 mmol) in water (2 mL) and CH3OH (5 mL) and the mixture was stirred at room temperature overnight. The reaction was quenched by addition of excess 60% aqueous acetic acid. After 30 minutes, the mixture was diluted with water, concentrated to remove CH3OH and lyophilized. The resulting powder (100 mg) was chromatographed on reverse phase silica gel [10 g, flash, stepwise gradient elution: water (200 mL), 10% CH3OH in water (v/v, 100 mL), 20% CH3OH in water (v/v, 100 mL), 10-mL fractions]. Fractions containing the product were combined, concentrated under reduced pressure and lyophilized to give oxanosine: 16 mg (89%). |
Here is a chemical reaction formula: Reactants are:m3:C(C1=CC=CC=C1)OC(=O)N=C=S;m1_m2_m4:C(C1=CC=CC=C1)OC(=O)N=C=S;m1_m2_m4:C1(=CC=CC=C1)C(C1=CC=CC=C1)OC(=O)C=1N=CN(C1N)[C@H]1[C@H](OC(C)=O)[C@H](OC(C)=O)[C@H](O1)COC(C)=O, Reagents are:m1_m2_m4:C(Cl)Cl, and Products are 0:C1(=CC=CC=C1)C(C1=CC=CC=C1)OC(=O)C=1N=CN(C1NC(=S)NC(=O)OCC1=CC=CC=C1)[C@H]1[C@H](OC(C)=O)[C@H](OC(C)=O)[C@H](O1)COC(C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Four portions of benzyloxycarbonyl isothiocyanate (Caution: stench, handle in a well ventilated hood only, crude, 2.0 g each, total 41 mmol) were added to a solution of 5-amino-1-(2,3,5-tris-O-acetyl-β-D-ribofuranosyl)-1H-imidazole-4-carboxylic acid diphenylmethyl ester (1.1 g, 2 mmol) in CH2Cl2 (10 mL) at 0 h, 6 h, 22 h and 30 h. The reaction mixture was stirred at room temperature under an argon atmosphere for a total of 46 h after the addition of the first portion of benzyloxycarbonyl isothiocyanate, then chromatographed on silica gel (100 g, column packed in CH2Cl2, 100-mL fractions), with CH2Cl2 (100 mL), followed by 25% EtOAc in CH2Cl2 as the eluant. Fractions 6 to 11 were combined, concentrated, and pumped under reduced pressure to give 1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-5-[[[[(phenylmethoxy)carbonyl]amino]thioxomethyl]amino]-1H-imidazole-4-carboxylic acid diphenylmethyl ester as a pale yellow foam: 1.46 g (98% yield); IR (CHCl3) 3405, 3250, 3200, 1750, 1738, 1600, and 1505 cm-1 ; HRMS [(+) FAB] m/z found 767.2060 [calcd for C37H36N4NaO11S, 767.1999 (M+Na+)], 745.2297 [calcd for C37H37N4O11S, 745.2180 (M+H+)]; NMR (CDCl3)δ2.04 (s, 3), 2.10 (s, 3), 2.13 (s, 3), 4.33 (m, 2), 4.39 (m, 1), 5.10 (s, 2), 5.35 (m, 1), 5.52 (m, 1), 5.87 (m, 1), 7.10 (s, 1), 7.32 (m, 15), 7.87 (s, 1), 8.16 (s, 1), 10.95 (s, 1); UV max (95% C2H5OH) 215 nm (sh, ε35000), 266 (13850). |
Here is a chemical reaction formula: Reactants are:m1:C1(=CC=CC=C1)COC(NC=1SC(C2=C(N1)N(C=N2)[C@H]2[C@H](O)[C@H](O)[C@H](O2)CO)=O)=O, Reagents are:m3:[Pd];m2:CN(C)C=O, and Products are 0:[C@@H]1([C@H](O)[C@H](O)[C@@H](CO)O1)N1C=NC=2C(=O)SC(N)=NC12, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of [3,7-dihydro-7-oxo-3-(β-D-ribofuranosyl)imidazo[4,5-d][1,3]thiazin-5-yl]carbamic acid phenylmethyl ester (170 mg, 0.39 mmol) in dry DMF (10 mL) was hydrogenated in the presence of 10% palladium on charcoal (200 mg) at room temperature and 50 psig for 6 h. Additional catalyst (200 mg) was added and hydrogenation continued for another 16 h. Catalyst was removed by filtration and was washed with DMF (10 mL) and ethanol (10 mL). The washing and filtrate were combined and concentrated under reduced pressure. The residue was dissolved in CH3OH and mixed with silica gel (3 g) and evaporated again to dryness. This silica gel sample was loaded on top of a silica gel column (30 g) packed in CHCl3 --CH3OH mixture, 4:1, v/v, and eluted with the same solvent, collecting 30-mL fractions. Fractions 7 to 12 were combined and concentrated, and pumped under reduced pressure to give pure 1-thiaguanosine: 90 mg (53%). 1-Thiaguanosine was crystallized from water-ethanol mixture to give needles: mp 212°-215° C. (dec); IR (KBr) 3415, 3385, 3300, 3190, 3105, 1695, 1662, 1635, and 1530 cm-1 ; HRMS [(+) FAB] m/z found 301.0597 [calcd for C10H13N4O5S, 301.0607 (M+H+)]; NMR (Me2SO-d6) δ3.53 (m, 1), 3.60 (m, 1), 3.86 (q, 1, J=4 Hz), 4.09 (m, 1), 4.38 (m, 1), 5.03 (t, 1, J=5 Hz), 5.20 (m, 1), 5.48 (d, 1, J=5 Hz), 5.80 (d, 1, J=6 Hz), 8.11 (s, 1), 8.34 (s, 2); UV max (95% C2H5OH) 207 nm (ε26750), 218 (sh, 24375), 264 (8000), 274 (5750), 323 (6725); (0.1N HCl) 210 nm (ε19000 ), 266 (8450), 277 (sh, 6400), 325 (6600); (pH 7 and pH 11) 209 nm (ε18400), 220 (sh, 18200), 264 (7600), 275 (sh, 5200), 325 (6450). |
Here is a chemical reaction formula: Reactants are:m3_m4:NC=1SC=CN1;m2:P(=O)(Cl)(Cl)Cl;m1_m6_m5:CN(C1=CC=CC=C1)C=O, Reagents are:m3_m4:C1(=CC=CC=C1)C;m1_m6_m5:NC=1SC=CN1;m1_m6_m5:C1(=CC=CC=C1)C, and Products are 0:S1C(=NC=C1)N=CN(C1=CC=CC=C1)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred suspension of N-methylformanilide (67.6 g; 0.50 mole), toluene (25 g) and 2-aminothiazole (2.0 g; 0.02 mole) was added phosphorus oxychloride (45.8 mL; 0.50 mole) over 15 minutes. The temperature was maintained below 45° C. during this addition. Stirring was continued for 10 minutes, after which time a hot solution of 2-aminothiazole (48.0 g; 0.48 mole) in toluene (250 g) was added at 60°-65° C. over 45 minutes. The reaction was allowed to cool to room temperature with stirring and was quenched by dropwise addition into a mixture of 30% sodium hydroxide (325 g) and ice (300 g). The organic phase was washed with a mixture of water (100 g), sodium chloride (10 g), and sodium bicarbonate (7.5 g), followed by a saturated solution of sodium chloride (125 g); the resultant organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated to yield 98.3 g of crude product. Vacuum distillation gave pure 1 (60.0 g; 55.3%) as a yellow oil: bp 177° C. @ 0.5 mm Hg. 1H-NMR (CDCl3) 8.72 (s, 1H), 7.4-6.9 (m, 7H), 3.50 (S, 3H); IR(neat) 3075, 2950, 1615, 1580, 1490, 1345, 1310, 1120; MS (m/e) 217 (M+, base). |
Here is a chemical reaction formula: Reactants are:m1:CN(C1=CC=CC=C1)C=O;m2:NC1=NC=CC=C1, Reagents are:, and Products are 0:N1=C(C=CC=C1)N=CN(C1=CC=CC=C1)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Prepared following the procedure of Example 1 from N-methylformanilide and 2-aminopyridine. Vacuum distillation of the crude product gave pure 3 as a pale yellow oil: bp 164°-165° C. @ 0.5 mm Hg. 1H-NMR (CDCl3) 8.94 (S, 1H), 8.30 (d, 1H, J=5 Hz), 7.6-6.9 (m,8H), 3.52 (S, 3H); IR(neat) 3045, 1620, 1580, 1555, 1500, 1460, 1435, 1235; MS (m/e) 211 (M+), 106 (base). |
Here is a chemical reaction formula: Reactants are:m1:C(C)N(C1=CC=CC=C1)C=O;m2:NC1=NC=CC=C1, Reagents are:, and Products are 0:N1=C(C=CC=C1)N=CN(C1=CC=CC=C1)CC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Prepared following the procedure of Example 1 from N-ethylformanilide and 2-aminopyridine. Vacuum distillation of the crude product gave pure 4 as a pale yellow oil: bp 164° C. @ 0.5 mm Hg. 1H-NMR (CDCl3) 8.83 (S, 1H), 8.30 (m,1H), 7.5-6.9 (m, 8H), 4.09 (q, 2H, J=7 Hz) 1.26 (t, 3H, J=7 Hz); IR(neat) 2990, 1620, 1570, 1500, 1460, 1440, 1390, 1230, 1130; MS (m/e) 225 (M+), 78 (base). |
Here is a chemical reaction formula: Reactants are:m1:C(C)OC(=O)N1CCC(CC1)(C1=CC(=C(C=C1)Cl)Cl)O;m2_m3:[OH-].[K+], Reagents are:m2_m3:C(CCC)O, and Products are 0:OC1(CCNCC1)C1=CC(=C(C=C1)Cl)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 64.2 g of 1-ethoxycarbonyl-4-hydroxy-4-(3,4-dichlorophenyl)piperidine (X-1) and a solution of 72.4 g of KOH in 700 ml of nBuOH is refluxed for 2 hours and evaporated. The reaction mixture is concentrated under reduced pressure and extracted with ethyl acetate. The organic layer is washed with water, dried and evaporated. The resulting crystalline residue is recrystallized from ethyl acetate to prepare 44.7 g (Yield: 90.0%) of the compound (II-1). mp. 144.5°-146.0° C. |
Here is a chemical reaction formula: Reactants are:m1_m2:CSCC=1CS[C@H]2N(C1C(=O)O)C(C2NC(C(=NOC)C=2N=C(SC2)NC(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=O)=O;m1_m2:FC(C(=O)O)(F)F, Reagents are:, and Products are 0:CSCC=1CS[C@H]2N(C1C(=O)O)C(C2NC(C(=NOC)C=2N=C(SC2)N)=O)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 6.15 g of the product of Step A and 61 ml of trifluoroacetic acid was stirred at 20° C. for 20 minutes and the mixture was evaporated under reduced pressure at 30° C. to a volume of 15 ml. 150 ml of ispropyl ether were added at 10° C. to the mixture which was then stirred at 20° C. for 15 minutes and was vacuum filtered. The 3.2 g of raw product were chromatographed over silica gel and were eluted with aqueous 2M sodium chloride solution containing 4% of 1M sodium bicarbonate solution. The raw product was dissolved in a mixture of 10 ml of eluant, 1.4 ml of aqueous 1M sodium bicarbonate solution, 1 ml of triethylamine and 1 ml of aqueous saturated sodium chloride solution and the solution was acidified to a pH of 3 by addition of 50% aqueous formic acid. The mixture was vacuum filtered and the product was washed with water and then with ether to obtain 0.99 g of syn isomer of 3-methylthiomethyl-7-[2-(2-amino-4-thiazolyl)-2-methoxyimino-acetamido]-ceph-3-eme-4-carboxylic acid. |