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Here is a chemical reaction formula: Reactants are:m3:C1(CCCCC1)N=C=NC1CCCCC1;m1:C[Si](C/C=C/CO)(C)C;m2:OC1=NC=C(C(=O)O)C=C1, Reagents are:m4:CN(C1=CC=NC=C1)C;m5:CN(C=O)C, and Products are 0:OC1=NC=C(C(=O)OC\C=C\C[Si](C)(C)C)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1.3 g of 4-trimethylsilyl-(E)-but-2-en-1-ol (synthesis described in J. Org. Chem. 1984, 49, 4092), 1.08 g of 6-hydroxy-nicotinic acid and 178 mg of 4-dimethylaminopyridine were placed in succession in 30 ml of abs. dimethylformamide. 1.77 g (1.1 eq.) of dicyclohexylcarbodiimide were added thereto at 0° and the mixture was left to react at room temperature overnight. The separated urea was filtered off, the filtrate was extracted with ethyl acetate, washed twice with H2O, dried over Na2 SO4 and the solvent was removed under reduced pressure. Flash chromatography on SiO2 (hexane/ethyl acetate=1/1) yielded 782 mg of 4-trimethylsilanyl-(E)-but-2-enyl 6-hydroxy-nicotinate as white crystals of m.p. 107°-110° (dec.). |
Here is a chemical reaction formula: Reactants are:m4:C(CCCC)OC=1C(=CC=2C(CCC(C2C1)(C)C)(C)C)C(=O)O;m1:BrC=1C=C2C(CCC(C2=CC1OCCCCC)(C)C)(C)C;m2:C(C)(C)(C)[Li];m3:C(=O)=O;m5:OC1=NC=C(C(=O)OCC2=CC=CC=C2)C=C1, Reagents are:, and Products are 0:C(CCCC)OC=1C(=CC=2C(CCC(C2C1)(C)C)(C)C)C(=O)OC1=NC=C(C(=O)OCC2=CC=CC=C2)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: In analogy to Example 1, by metallating 6-bromo-7-pentoxy-1,1,4,4-tetramethyl-1,2,3,4-tetrahydro-naphthalene with tert.butyl-lithium and reacting with carbon dioxide gas there was prepared 3-pentoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalene-2-carboxylic acid (m.p. 67°-68° C., from hexane). Reaction of this acid with benzyl 6-hydroxy-nicotinate gave benzyl 6-(3-pentoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-carbonyloxy)-nicotinate as a colorless oil. Subsequent hydrogenation yielded the desired end product 6-(3-pentoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl-carbonyloxy)-nicotinic acid in white crystals, m.p. 132°-133° C. (from diethyl ether/hexane). |
Here is a chemical reaction formula: Reactants are:m5_m2:C(CCC)[SnH](CCCC)CCCC;m1_m4:C12(CC3CC(CC(C1)C3)C2)C=2C=C(C(=O)OC3=NC=C(C(=O)OCC=C)C=C3)C=CC2O[Si](C)(C)C(C)(C)C;m3:Cl, Reagents are:m5_m2:[Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1;m1_m4:O1CCCC1, and Products are 0:C12(CC3CC(CC(C1)C3)C2)C=2C=C(C(=O)OC3=NC=C(C(=O)O)C=C3)C=CC2O[Si](C)(C)C(C)(C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 100 mg of this ester were dissolved in 5 ml of absolute tetrahydrofuran and treated under argon with 104 mg of tetrakis-(triphenylphosphine)-palladium and 61 mg of tributyltin hydride. After stirring at room temperature for 30 min., the reaction mixture was poured on to ice/saturated ammonium chloride solution, acidified with 1N hydrochloric acid and extracted with ethyl acetate. The dark oil obtained after drying and evaporation was purified by chromatography (RP18-LiChroprep, acetonitrile) and recrystallization from ethyl acetate. There were obtained 21 mg of 6-[3-adamantan-1-yl-4-(tert-butyl-dimethyl-silanyloxy)-benzoyloxy]-nicotinic acid in colorless crystals, m.p. 188°-190° C. |
Here is a chemical reaction formula: Reactants are:m1_m3_m2:C[C@@H]1CC[C@H]2[C@H]([C@H](O[C@H]3[C@@]24[C@H]1CCC(O3)(OO4)C)O)C;m1_m3_m2:CN=C=O, Reagents are:m1_m3_m2:C(Cl)Cl, and Products are 0:C[C@@H]1CC[C@H]2[C@H]([C@H](O[C@H]3[C@@]24[C@H]1CCC(O3)(OO4)C)O)C.CNC([O-])=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of dihydroqinghaosu (284 mg, 1 mmol) in dry CH2Cl2 (6 ml) and methyl isocyanate (63 mg, 1.1 mmol) was refluxed for ca. 2 days. The solution was filtered and evaporated in vacuo at 40° C. to give a solid, which was chromatographed on a silica-gel column with petroleumether/AcOEt 8:2. The fraction obtained was evaporated to give a white powder (217.6 mg). |
Here is a chemical reaction formula: Reactants are:m0_m1_m2:C[C@@H]1CC[C@H]2[C@H]([C@H](O[C@H]3[C@@]24[C@H]1CCC(O3)(OO4)C)O)C;m0_m1_m2:[N+](=O)([O-])C=1C=C(C=CC1)N=C=O, Reagents are:, and Products are 0:C[C@@H]1CC[C@H]2[C@H]([C@H](O[C@H]3[C@@]24[C@H]1CCC(O3)(OO4)C)O)C.[N+](=O)([O-])C=1C=C(C=CC1)NC(=O)[O-], please give me the reaction condition of this formula. | The condition of this chemical reaction is: The title compound was similarly prepared from dihydroqinghaosu and m-nitrophenyl isocyanate as Example 3. |
Here is a chemical reaction formula: Reactants are:m1_m3:C1(=CC=CC=C1)C1CCC(CC1)=O;m2:[BH4-].[Na+], Reagents are:m1_m3:CO, and Products are 0:C1(=CC=CC=C1)C1CCC(CC1)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 31.4 g (0.18 mol) of 4-phenylcyclohexanone in 500 ml of absolute methanol, which is cooled to -10° C., are added 6.8 g (0.18 mol) of sodium borohydride in batches with stirring. The reaction mixture is allowed to react for 0.5 hours at -10° C. and for 3 hours at ambient temperature and then evaporated down in vacuo. The residue remaining is mixed with water and acidified with 2N hydrochloric acid. The suspension formed is stirred for 1 hour and the crystalline product is suction filtered, dried and recrystallised from diisopropylether. 21 g (66% of theory) of 4-phenylcyclohexanol are obtained, melting point: 112°-114° C. |
Here is a chemical reaction formula: Reactants are:m3:BrCC1=CC=C(C#N)C=C1;m1_m5_m2:[H-].[Na+];m1_m5_m2:N1C(NCC1)=O;m4:O, Reagents are:m1_m5_m2:CN(C=O)C, and Products are 0:O=C1N(CCN1CC1=CC=C(C#N)C=C1)CC1=CC=C(C#N)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To sodium hydride (2.4 g, 60 mmol) in dimethylformamide (50 mL) at 0° C. was added imidazolin-2-one (2.6 g, 30 mmol). After stirring for 20 minutes 4-(bromomethyl)benzonitrile (13 g, 66 mmol) was added and the mixture was warmed to ambient temperature. After stirring for 1 hour the reaction was poured into water and a solid formed. The solid was filtered to give 4,4'-[(2-oxoimidazolin-1,3-diyl)bis(methylene)]-bis(benzonitrile). NMR (CDCl3) 7.65 (d,4), 7.4 (d,4), 4.45 (s,4), 3.2 (s,4) ppm. |
Here is a chemical reaction formula: Reactants are:m3_m1_m2:NC(=O)N;m3_m1_m2:CN(C1=CC=C(C=C1)C(C(=O)C1=CC=CC=C1)O)C, Reagents are:m3_m1_m2:C(C)(=O)O, and Products are 0:CN(C1=CC=C(C=C1)C=1NC(NC1C1=CC=CC=C1)=O)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To acetic acid (2 mL) was added urea (0.6 g, 10 mmol) and 2-(4-dimethylaminophenyl)-2-hydroxy-1-phenylethanone (2.6 g, 10 mmol). After stirring for 2 hours at 120° C., the reaction was cooled to ambient temperature. The resulting solid was filtered, washed with ether, and dried in vacuo to give 4-(4-dimethylaminophenyl)-2,3-dihydro-5-phenyl-1H-imidazol-2-one; NMR (CDCl3) 10.98 (s,2), 7.5 (m,4), 7.4 (m,5), 3.18 (s,6) ppm. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:C1(=CC=CC=C1)C=1NC(NC1C1=CC=CC=C1)=O;m1_m2_m3_m4:BrCC=1C=C(C#N)C=CC1;m1_m2_m3_m4:[H-].[Na+], Reagents are:m1_m2_m3_m4:CN(C=O)C, and Products are 0:C1(=CC=CC=C1)C=1NC(N(C1C1=CC=CC=C1)CC=1C=C(C#N)C=CC1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: In a manner similar to Preparation 1 above, 2,3-dihydro-4,5-diphenyl-1H-imidazol-2-one (1.2 g, 5 mmol) was reacted with 3-(bromomethyl)benzonitrile (0.39 g, mmol) and sodium hydride (0.18 g, 5 mmol) in dimethylformamide (20 mL) to give 3-[(2,3-dihydro-4,5-diphenyl-2-oxo-1H-imidazol-1-yl)methyl]benzonitrile after chromatography on silica; NMR (DMSO-d6) 11.02 (s,1), 7.4 (m,4), 7.3 (m,2), 7.2 (m,7), 4.75 (s,2) ppm. |
Here is a chemical reaction formula: Reactants are:m4:Cl;m1_m5_m2_m6:C1(=CC=CC=C1)C=1NC(NC1C1=CC=CC=C1)=O;m1_m5_m2_m6:[H-].[Na+];m3_m7:BrCC=1C=C(C(=O)OC)C=CC1, Reagents are:m1_m5_m2_m6:CN(C)C=O;m1_m5_m2_m6:CN(C)C=O;m3_m7:CN(C)C=O, and Products are 0:COC(=O)C=1C=C(C=CC1)CN1C(NC(=C1C1=CC=CC=C1)C1=CC=CC=C1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To 2,3-dihydro-4,5-diphenyl-1H-imidazol-2-one (4.76 g, 20 mmol) in 50 mL DMF was added to a suspension of NaH (0.8 g, 20 mmol) in 25 mL DMF. The suspension was stirred at ambient temperatures for 30 minutes, then heated to 50° C. for 30 minutes. A solution of methyl 3-bromomethylbenzoate (2.86 g, 12.5 mmol) in 20 mL DMF was then added and the reaction stirred for 10 min at 50° C. The mixture was poured into 1N HCl, filtered, washed with water and dried. Chromatography on silica gel (2% EtOH in 7:3 methylene chloride/ethyl acetate) afforded 1.2 g of 3-(3-methoxycarbonylphenyl)methyl-4,5-diphenyl-1H-imidazol-2-one as a white solid. |
Here is a chemical reaction formula: Reactants are:m2:BrCC1=CC=C2C=CC(=CC2=C1)C#N;m1:C1(=CC=CC=C1)C=1NC(N(C1C1=CC=CC=C1)CC=1C=C(C#N)C=CC1)=O, Reagents are:, and Products are 0:C(#N)C=1C=C(C=CC1)CN1C(N(C(=C1C1=CC=CC=C1)C1=CC=CC=C1)CC1=CC=C2C=CC(=CC2=C1)C#N)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: In a manner similar to Preparation 2 above, 3-[(2,3-dihydro-4,5-diphenyl-2-oxo-1H-imidazol-1-yl)methyl]benzonitrile was reacted with 7-(bromomethyl)naphthalene-2-carbonitrile to give 7-[[3-(3-cyanophenyl)methyl-2,3-dihydro-4,5-diphenyl-2-oxo-1H-imidazol-1-yl]methyl]naphthalene-2-carbonitrile; NMR (CDCl3) 8.05 (s, 1), 7.9 (d,1), 7.85 (d,1), 7.55 (m,3), 7.4 (m,2), 7.2 (m,9), 7.0 (m,3), 5.1 (s,2), 4.95 (s,2) ppm. |
Here is a chemical reaction formula: Reactants are:m2_m6_m3_m4:C(C=C)(=O)OC;m2_m6_m3_m4:C1(=C(C=CC=C1)P(C1=C(C=CC=C1)C)C1=C(C=CC=C1)C)C;m2_m6_m3_m4:C(C)N(CC)CC;m1_m5:BrC=1C=C2CCC(CC2=CC1)N(CCC)CCC, Reagents are:m2_m6_m3_m4:C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-];m7:O;m1_m5:CN(C=O)C, and Products are 0:COC(\C=C\C=1C=C2CCC(CC2=CC1)N(CCC)CCC)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 3.1 g (0.01 mol) of 6-bromo-2-(N,N-dipropylamino)-1,2,3,4-tetrahydronaphthalene are dissolved in 50 ml of dimethylformamide. There are added in succession to that solution 0.94 g (0.011 mol) of methyl acrylate, 22.4 mg (0.1 mmol) of palladium acetate, 121 mg (0.4 mmol) of tri-ortho-tolylphosphine and 1.6 ml (0.011 mol) of triethylamine. The mixture is heated at 125°-130° C. for 3 h 30 min. with stirring, cooled, poured into 700 ml of water, extracted with ethyl acetate and washed with a solution of LiCl. After acid to base change, 0.9 g of the expected product is obtained. |
Here is a chemical reaction formula: Reactants are:m1_m4_m2_m3:OC1=C(C(=O)OC)C=CC(=C1)O;m1_m4_m2_m3:C(=O)([O-])[O-].[K+].[K+];m1_m4_m2_m3:C(C1=CC=CC=C1)Br, Reagents are:m1_m4_m2_m3:CC(=O)C, and Products are 0:C(C1=CC=CC=C1)OC1=CC(=C(C(=O)OC)C=C1)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred, 0° C. solution of methyl 2,4-dihydroxybenzoate (50 g, 300 mmol) in acetone (1000 mL) was added K2CO3 (150 g, 1000 mmol) and benzyl bromide (330 mmol, 39 mL). The solution was allowed to warm to ambient temperature over 48 h. The reaction solution was filtered through celite and the acetone solution stripped down under reduced pressure. The crude oil was dissolved in EtOAc (1000 mL) and washed with water (250 mL), and saturated aqueous NaHCO3 (500 mL). The EtOAc layer was dried (MgSO4), filtered, and the EtOAc was removed under reduced pressure. The crude product was purified by pressurized silica gel column chromatography using 5:1 hexanes:EtOAc. Evaporation of the hexanes:EtOAc mixture gave the desired methyl 4-benzyloxy-2-hydroxybenzoate as a white powder. |
Here is a chemical reaction formula: Reactants are:m1_m4_m2_m3:C(C1=CC=CC=C1)OC1=CC(=C(C(=O)OC)C=C1)O;m1_m4_m2_m3:[H-].[Na+];m1_m4_m2_m3:CI, Reagents are:m1_m4_m2_m3:CN(C)C=O, and Products are 0:C(C1=CC=CC=C1)OC1=CC(=C(C(=O)OC)C=C1)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred, 0° C. solution of methyl 4-benzyloxy-2-hydroxybenzoate (12 g, 46 mmol) in DMF (150 mL) was added NaH (2.76 g, 69 mmol) and methyl iodide (7.2 mL, 116 mmol). The solution was allowed to warm to ambient temperature overnight with stirring. The reaction mixture was poured onto ice and the resulting aqueous solution extracted with Et2O (3×200 mL). The organic phase was dried (MgSO4), filtered and the Et2O removed under reduced pressure. The crude white solid was purified by pressurized silica gel column chromatography using 4:1 hexanes:EtOAc. Evaporation of the hexanes:EtOAc mixture gave the desired methyl 4-benzyloxy-2-methoxybenzoate as a white powder. |
Here is a chemical reaction formula: Reactants are:m4:Cl;m1_m5_m2_m3:OC1=CC(=C(C(=O)OC)C=C1)OC;m1_m5_m2_m3:O;m1_m5_m2_m3:O[Li].O, Reagents are:m1_m5_m2_m3:C1CCOC1, and Products are 0:OC1=CC(=C(C(=O)O)C=C1)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred solution of methyl 4-hydroxy-2-methoxybenzoate (11 g, 60 mmol) in THF:H2O (100 mL:10 mL) was added LiOH.H2O (3 g, 71 mmol). The solution was stirred over 24 h and then made slightly acidic (pH 5) with 10% HCl (approx 15 mL). The reaction solution was extracted with CH2Cl2 (3×50 mL). The organic phase was dried (MgSO4) and filtered. The solvent was evaporated under reduced pressure to afford the 4-hydroxy-2-methoxybenzoic acid as a clean white foam. |
Here is a chemical reaction formula: Reactants are:m1_m3_m2:OC1=CC(=C(C(=O)OC)C=C1)OC;m1_m3_m2:[O-]S(=O)(=O)C(F)(F)F.ClC=1C=[N+](C=C(C1)Cl)F, Reagents are:m1_m3_m2:C(Cl)Cl, and Products are 0:FC=1C(=CC(=C(C(=O)OC)C1)OC)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred solution of the methyl 4-hydroxy-2-methoxybenzoate (1 g, 5 mmol, from Step 3) in CH2Cl2 (20 mL) was added 3,5-dichloro-1-fluoropyridinium triflate (2.25 g, 6 mmol). The solution was refluxed for 48 h and then cooled to ambient temperature and stripped down under reduced pressure. The crude oil was purified by pressurized silica gel column chromatography using 99:1 CH2Cl2 :MeOH. Evaporation of the CH2Cl2 :MeOH mixture gave the desired methyl 5-fluoro-4-hydroxy-2-methoxybenzoate as a white powder. |
Here is a chemical reaction formula: Reactants are:m3_m4_m6:O1CCC(CC1)O;m3_m4_m6:N(=NC(=O)OCC)C(=O)OCC;m1_m5_m2:OC1=CC(=C(C(=O)OC)C=C1)OC;m1_m5_m2:C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1, Reagents are:m3_m4_m6:C1CCOC1;m1_m5_m2:C1CCOC1, and Products are 0:O1CCC(CC1)C(=O)OC1=CC(=C(C(=O)OC)C=C1)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred solution of methyl 4-hydroxy-2-methoxybenzoate (713 mg, 3.92 mmol) in dry THF (7.5 mL) was added triphenylphosphine (1.42 g, 5.4 mmol) and the solution was cooled to 0° C. A 2.5 mL volume of tetrahydro-4H-pyran-4-ol (466 mL, 4.90 mmol) and diethyl azodicarboxylate (850 μL, 5.4 mmol) in THF was added dropwise via addition funnel over 0.5 h. The reaction was filtered and the solvent was removed under reduced pressure. The residue was chromatographed on a silica gel column packed in 60:40 hexanes:EtOAc and eluted with same. The appropriate fractions were combined and the solvent removed under reduced pressure to afford methyl 4-(4-tetra-hydropyranoyloxy)-2-methoxy-benzoate. |
Here is a chemical reaction formula: Reactants are:m1_m4_m2_m3:O1CCC(CC1)C(=O)OC1=CC(=C(C(=O)OC)C=C1)OC;m1_m4_m2_m3:O;m1_m4_m2_m3:O[Li].O, Reagents are:m1_m4_m2_m3:C1CCOC1, and Products are 0:O1CCC(CC1)C(=O)OC1=CC(=C(C(=O)O)C=C1)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred solution of methyl 4-(4-tetrahydropyranoyloxy)-2-methoxy-benzoate (369 mg, 1.38 mmol) in THF:H2O (2.5 mL: 0.5 mL) was added LiOH.H2O (116.4 mg, 2.77 mmol). The reaction was heated to 45° C. over 12 h and then cooled to ambient temperature. The solvent was removed under reduced pressure. The crude solid was passed through a small plug of silca gel packed in 80:20 hexanes:EtOAc and eluted with 50:50 hexanes:EtOAc. The solvent was removed under reduced pressure to afford 4-(4-tetrahydropyranoyloxy)-2-methoxy-benzoic acid as a foam. |
Here is a chemical reaction formula: Reactants are:m1_m4_m2_m3:C1(CCC2=CC=CC=C12)C(=O)OC1=CC(=C(C(=O)OC)C=C1)OC;m1_m4_m2_m3:O;m1_m4_m2_m3:O[Li].O, Reagents are:m1_m4_m2_m3:C1CCOC1, and Products are 0:C1(CCC2=CC=CC=C12)C(=O)OC1=CC(=C(C(=O)O)C=C1)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred solution of methyl 4-(1-indanoyloxy)-2-methoxy-benzoate (125 mg, 0.43 mmol) in THF:H2O (1 mL: 0.2 mL) was added LiOH.H2O (35.2 mg, 0.84 mmol). The reaction was heated to 45° C. over 12 h and then cooled to ambient temperature. The solvent was removed under reduced pressure. The crude solid was passed through a small plug of silca gel packed in 80:20 hexanes:EtOAc and eluted with 50:50 hexanes:EtOAc. The solvent was removed under reduced pressure to afford 4-(1-indanoyloxy)-2-methoxy-benzoic acid as a foam. |
Here is a chemical reaction formula: Reactants are:m1_m5_m2:OC1=CC(=C(C(=O)OC)C=C1)OC;m1_m5_m2:C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1;m3_m4_m6:C1(=CC=CC=C1)[C@H]1[C@@H](CCCC1)O;m3_m4_m6:N(=NC(=O)OCC)C(=O)OCC, Reagents are:m1_m5_m2:C1CCOC1;m3_m4_m6:C1CCOC1, and Products are 0:C1(=CC=CC=C1)[C@@H]1[C@@H](CCCC1)C(=O)OC1=CC(=C(C(=O)OC)C=C1)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred solution of methyl 4-hydroxy-2-methoxybenzoate (310 mg, 1.7 mmol) in dry THF (1.25 mL) was added triphenylphosphine (446 mg, 1.7 mmol) and the solution was cooled to 0° C. A 500 mL volume of trans-2-phenyl-1-cyclohexanol (200 mg, 1.35 mmol) and diethyl azodicarboxylate (319 μL, 2.02 mmol) in THF was added dropwise via addition funnel over 0.5 h. The reaction was filtered and the solvent was removed under reduced pressure. The residue was chromatographed on a silica gel column packed in 92:8 hexanes:EtOAc and eluted with same. The appropriate fractions were combined and the solvent removed under reduced pressure to afford methyl 4-(cis-2-phenyl-1-cyclohexanoyloxy)-2-methoxybenzoate. |
Here is a chemical reaction formula: Reactants are:m1_m4_m2_m3:C1(=CC=CC=C1)[C@@H]1[C@@H](CCCC1)C(=O)OC1=CC(=C(C(=O)OC)C=C1)OC;m1_m4_m2_m3:O;m1_m4_m2_m3:O[Li].O, Reagents are:m1_m4_m2_m3:C1CCOC1, and Products are 0:C1(=CC=CC=C1)[C@@H]1[C@@H](CCCC1)C(=O)OC1=CC(=C(C(=O)O)C=C1)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred solution of methyl 4-(cis-2-phenyl- 1-cyclohexanoyloxy)-2-methoxybenzoate (230 mg, 0.64 mmol) in THF:H2O (5 mL:1 mL) was added LiOH.H2O (113.5 mg, 2.7 mmol). The reaction was heated to 45° C. over 12 h and then cooled to ambient temperature. The solvent was removed under reduced pressure. The crude solid was passed through a small plug of silca gel packed in 90:10 CH2Cl2 :MeOH(NH3) and eluted with same. The solvent was removed under reduced pressure to afford 4-(cis-2-phenyl-1-cyclohexanoyloxy)-2-methoxy-benzoic acid as a foam. |
Here is a chemical reaction formula: Reactants are:m1_m3_m2:OCC=1C(=NC=CC1)C;m1_m3_m2:O=S(Cl)Cl, Reagents are:m1_m3_m2:C(Cl)Cl, and Products are 0:ClCC=1C(=NC=CC1)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred solution of 3-hydroxymethyl-2-methylpyridine from Step 1 above (1.00 g, 8.13 mmol) in 40 mL of CH2Cl2 at ambient temperature was added SOCl2 (9.0 mL, 123 mmol). The reaction mixture was stirred for 4 hours, and the solvent and excess SOCl2 were evaporated under reduced pressure. The residue was partitioned between CH2Cl2 and saturated aqueous NaHCO3. The organic layer was separated, and the aqueous layer was washed with additional CH2 Cl2 (2×40 mL). The combined organic layers were evaporated under reduced pressure to give 3-chloromethyl-2-methylpyridine as a pale yellow-brown solid (TLC: Rf =0.85 in 5% MeOH in CH2Cl2 ; FAB MS m/z 142 (M+ +H)). |
Here is a chemical reaction formula: Reactants are:m1_m3_m2:ClCC=1C(=NC=CC1)C;m1_m3_m2:ClC=1C=C(C(=O)OO)C=CC1, Reagents are:m1_m3_m2:C(Cl)(Cl)Cl, and Products are 0:ClCC=1C(=[N+](C=CC1)[O-])C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred solution of 3-chloromethyl-2-methylpyridine from Step 2 above (0.50 g; 3.5 mmol) in CHCl3 (40 mL) was added m-chloroperoxybenzoic acid (1.1 g of 55:45 mCPBA:mCBA; 3.5 mmol). After 1.5 h, TLC analysis indicated complete conversion to a lower Rf product. The solution was extracted with equal volumes of saturated aqueous NaHCO3 and water, dried (MgSO4), filtered, and evaporated under reduced pressure. The residue was purified by pressurized silica gel column chromatography using 97:3 CH2Cl2 :MeOH as eluant. 3-Chloromethyl-2-methylpyridine N-oxide was obtained as a solid (TLC: Rf =0.30 (97:3 CH2Cl2 :MeOH); FAB MS m/z 158 (M+ +H)). |
Here is a chemical reaction formula: Reactants are:m3_m4_m6:O1CCC(C2=CC=CC=C12)O;m3_m4_m6:N(=NC(=O)OCC)C(=O)OCC;m1_m5_m2:OC1=CC(=C(C(=O)OC)C=C1)OC;m1_m5_m2:C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1, Reagents are:m3_m4_m6:C1CCOC1;m1_m5_m2:C1CCOC1, and Products are 0:O1CCC(C2=CC=CC=C12)C(=O)OC1=CC(=C(C(=O)OC)C=C1)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred solution of methyl 4-hydroxy-2-methoxybenzoate (364 mg, 2.0 mmol) in dry THF (1.25 mL) was added triphenylphosphine (525 mg, 2.0 mmol) and the solution was cooled to 0° C. A 500 mL volume of 4-chromanol (200 mg, 1.33 mmol) and diethyl azodicarboxylate (315 mL, 2.0 mmol) in THF was added dropwise via syringe over 0.5 h. The reaction was filtered and the solvent was removed under reduced pressure. The residue was chromatographed on a silica gel column packed in 92:8 hexanes:EtOAc and eluted with same. The appropriate fractions were combined and the solvent removed under reduced pressure to afford methyl 4-(4-chromanoyloxy)-2-methoxybenzoate. |
Here is a chemical reaction formula: Reactants are:m1_m4_m2_m3:O1CCC(C2=CC=CC=C12)C(=O)OC1=CC(=C(C(=O)OC)C=C1)OC;m1_m4_m2_m3:O;m1_m4_m2_m3:O[Li].O, Reagents are:m1_m4_m2_m3:C1CCOC1, and Products are 0:O1CCC(C2=CC=CC=C12)C(=O)OC1=CC(=C(C(=O)O)C=C1)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred solution of methyl 4-(4-chromanoyloxy)-2-methoxybenzoate (260 mg, 0.82 mmol) in THF:H2O (4 mL:0.8 mL) was added LiOH.H2O (172 mg, 4.1 mmol). The reaction was heated to 45° C. over 12 h and then cooled to ambient temperature. The solvent was removed under reduced pressure. The crude solid was passed through a small plug of silca gel packed in 90:10 CH2Cl2 :MeOH(NH3) and eluted with same. The solvent was removed under reduced pressure to afford 4-(4-chromanoyloxy)-2-methoxybenzoic acid as a foam. |
Here is a chemical reaction formula: Reactants are:m1_m3:CC=1C=NC=2CC(CC(C2C1)=O)(C)C;m2:[BH4-].[Na+], Reagents are:m1_m3:CO, and Products are 0:CC=1C=NC=2CC(CC(C2C1)O)(C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A stirred solution of 5,6,7,8-tetrahydro-3,7,7-trimethylquinoline-5-one (240 mg, 1.3 mmol) in MeOH (6.5 mL) was cooled to 0° C. under Argon and treated with NaBH4 (48 mg, 1.3 mmol). The reaction was stirred over 14 h and allowed to warm to ambient temperature. The solvent was removed under reduced pressure and the crude oil that was chromatographed on a silica gel column packed in 95:5 EtOAc:hexanes and eluted with same. The appropriate fractions were combined and the solvent was removed under reduced pressure to give 5,6,7,8-tetrahydro-3,7,7-trimethylquinoline-5-ol. |
Here is a chemical reaction formula: Reactants are:m1_m3:[Li+].C(C)C1=C(C(=O)[O-])C=CC=N1;m2:[H-].[Al+3].[Li+].[H-].[H-].[H-], Reagents are:m1_m3:C1CCOC1, and Products are 0:C(C)C1=NC=CC=C1CO, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The 2-ethyl nicotinic acid lithium salt (5 g, 3.18 mmol) in distilled THF (400 mL) under nitrogen was cooled to 0° C. and lithium aluminum hydride (1M in THF) (25 mL) was added dropwise. The reaction was stirred for 3 hours at room temperature then cooled to 0° C. and quenched with EtOAc (949 μL), then H2O (949 μL), then 15% NaOH (949 μL), followed by H2O (2.8 mL). The solution was filtered and the solvent removed under reduced pressure. Toluene was added and the solvent was removed under reduced pressure to give the desired 2-ethyl-3 -hydroxymethylpyridine. |
Here is a chemical reaction formula: Reactants are:m2:S(=O)(Cl)Cl;m1_m3:C(C)C1=NC=CC=C1CO, Reagents are:m1_m3:C(Cl)Cl, and Products are 0:C(C)C1=NC=CC=C1CCl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The 2-ethyl-3-hydroxymethylpyridine (2.3 g, 16.8 mmol) was dissolved in CH2Cl2 (100 mL) and cooled under nitrogen to 0° C. and thionyl chloride (7.0 mL) was slowly added and the reaction was stirred for 3 hours. The solvent was removed under reduced pressure and the residue was partitioned between CH2Cl2 (100 mL) and saturated aqueous sodium bicarbonate (100 mL). The organic layer was dried with MgSO4, filtered, and the solvent removed under reduced pressure to give the desired 2-ethyl-3-chloromethylpyridine. |
Here is a chemical reaction formula: Reactants are:m1_m3:C(C)C1=NC=CC=C1CCl;m2:ClC1=CC(=CC=C1)C(=O)OO, Reagents are:m1_m3:C(Cl)(Cl)Cl, and Products are 0:C(C)C1=[N+](C=CC=C1CCl)[O-], please give me the reaction condition of this formula. | The condition of this chemical reaction is: The 2-ethyl-3-chloromethylpyridine (2.4 g, 15.4 mmol) was dissolved in CHCl3 (100 mL) and cooled under nitrogen to 0° C. and m-chloroperbenzoic acid (55%, 4.2 g) was added in small portions. The reaction was stirred for 2 hours. The reaction was extracted twice with saturated aqueous sodium bicarbonate (100 mL). The organic phase was dried with MgSO4, filtered and the solvent was removed under reduced pressure. The residue was chromatographed on silica gel packed in 98:2 CH2Cl2 :MeOH and eluted with the same. The appropriate fractions were combined and the solvent removed under reduced pressure the give the desired 2-ethyl-3-chloromethylpyridine-N-oxide. |
Here is a chemical reaction formula: Reactants are:m1_m3:C(C)(C)C1=NC=CC=C1C(=O)OCC;m2:[H-].[Al+3].[Li+].[H-].[H-].[H-], Reagents are:m1_m3:C1CCOC1, and Products are 0:C(C)(C)C1=NC=CC=C1CO, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The 2-isopropyl-3-carboethoxypyridine (400 mg, 2 mmol) in distilled THF (50 mL) under nitrogen was cooled to 0° C. and lithium aluminum hydride (1M in THF) (2.07 mL) was added dropwise. The reaction was stirred for 18 hours at room temperature then cooled to 0° C. and quenched with EtOAc (100 μL), then H2O (100 μL), then 15% NaOH (100 μL), followed by H2O (300 μL). The mixture was filtered and the solvent was removed under reduced pressure. Toluene was added and the solvent was removed under reduced pressure to give the desired 2-isopropyl-3-hydroxymethylpyridine. |
Here is a chemical reaction formula: Reactants are:m1_m3:C(C)(C)C1=NC=CC=C1CO;m2:S(=O)(Cl)Cl, Reagents are:m1_m3:C(Cl)Cl, and Products are 0:C(C)(C)C1=NC=CC=C1CCl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The 2-isopropyl-3-hydroxymethylpyridine (240 mg, 1.59 mmol) was dissolved in CH2Cl2 (15 mL) and cooled under nitrogen to 0° C. and thionyl chloride (1.0 mL) was slowly added and the reaction was stirred for 3 hours. The solvent was removed under reduced pressure and the residue was partitioned between CH2Cl2 and saturated sodium bicarbonate. The organic layer was dried with MgSO4, filtered and the solvent removed under reduced pressure to give the desired 2-isopropyl-3-chloromethylpyridine. The 2-isopropyl-3-chloromethylpyridine (65 mg, 0.383 mmol) was dissolved in CHCl3 (10 mL) and cooled under nitrogen to 0° C. and m-chloroperbenzoic acid (55%, 150 mg) was added in small portions. The reaction was stirred for 2 hours. The solution was extracted with saturated aqueous sodium bicarbonate (2×5 mL). The organic phase was dried with MgSO4, filtered, and the solvent removed under reduced pressure. The residue was chromatographed on silica gel packed in 99:1 CH2Cl2 :MeOH and eluted with same. The appropriate fractions were combined and the solvent removed under reduced pressure to give the desired 2-isopropyl-3-chloromethylpyridine-N-oxide. |
Here is a chemical reaction formula: Reactants are:m1_m3:C(C)(C)C1=NC=CC=C1CCl;m2:ClC1=CC(=CC=C1)C(=O)OO, Reagents are:m1_m3:C(Cl)(Cl)Cl, and Products are 0:C(C)(C)C1=[N+](C=CC=C1CCl)[O-], please give me the reaction condition of this formula. | The condition of this chemical reaction is: The 2-isopropyl-3-hydroxymethylpyridine (240 mg, 1.59 mmol) was dissolved in CH2Cl2 (15 mL) and cooled under nitrogen to 0° C. and thionyl chloride (1.0 mL) was slowly added and the reaction was stirred for 3 hours. The solvent was removed under reduced pressure and the residue was partitioned between CH2Cl2 and saturated sodium bicarbonate. The organic layer was dried with MgSO4, filtered and the solvent removed under reduced pressure to give the desired 2-isopropyl-3-chloromethylpyridine. The 2-isopropyl-3-chloromethylpyridine (65 mg, 0.383 mmol) was dissolved in CHCl3 (10 mL) and cooled under nitrogen to 0° C. and m-chloroperbenzoic acid (55%, 150 mg) was added in small portions. The reaction was stirred for 2 hours. The solution was extracted with saturated aqueous sodium bicarbonate (2×5 mL). The organic phase was dried with MgSO4, filtered, and the solvent removed under reduced pressure. The residue was chromatographed on silica gel packed in 99:1 CH2Cl2 :MeOH and eluted with same. The appropriate fractions were combined and the solvent removed under reduced pressure to give the desired 2-isopropyl-3-chloromethylpyridine-N-oxide. |
Here is a chemical reaction formula: Reactants are:m2:[H-].[Al+3].[Li+].[H-].[H-].[H-];m1_m3:CC1=NC=CC(=C1C(=O)OCC)C, Reagents are:m1_m3:C1CCOC1, and Products are 0:CC1=NC=CC(=C1CO)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The 2,4-dimethyl-3-carboethoxypyridine (11.3 g, 63.1 mmol) in distilled THF (375 mL) under nitrogen was cooled to 0° C. and lithium aluminum hydride (1M in THF, 63.1 mL) was added dropwise. The reaction was stirred for 18 hours at room temperature then cooled to 0° C. and quenched with EtOAc (2.5 mL), then H2O (2.5 mL), then 15% NaOH (2.5 mL), followed by H2O (7.5 mL). The solution was filtered and the solvent removed under reduced pressure to give the desired 2,4-dimethyl-3-hydroxymethylpyridine. |
Here is a chemical reaction formula: Reactants are:m2:S(=O)(Cl)Cl;m1_m3:CC1=NC=CC(=C1CO)C, Reagents are:m1_m3:C(Cl)Cl, and Products are 0:CC1=NC=CC(=C1CCl)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The 2,4-dimethyl-3-hydroxymethylpyridine (19.2 g, 140 mmol) was dissolved in CH2Cl2 (800 mL) and cooled under nitrogen to 0° C. and thionyl chloride (125 mL) was slowly added and the reaction was stirred for 18 hours. The solvent was removed under reduced pressure and the residue was partitioned between CH2Cl2 and saturated aqueous sodium bicarbonate. The organic layer was dried with MgSO4, filtered and the solvent removed under reduced pressure to give the desired 2,4-dimethyl-3-chloromethylpyridine. |
Here is a chemical reaction formula: Reactants are:m1_m3:CC1=NC=CC(=C1CCl)C;m2:ClC1=CC(=CC=C1)C(=O)OO, Reagents are:m1_m3:C(Cl)(Cl)Cl, and Products are 0:CC1=[N+](C=CC(=C1CCl)C)[O-], please give me the reaction condition of this formula. | The condition of this chemical reaction is: The 2,4-dimethyl-3-chloromethylpyridine (21.5 g, 138 mmol) was dissolved in CHCl3 (800 mL) and cooled under nitrogen to 0° C. and m-chloroperbenzoic acid (55%, 35 g) was added in small portions. The reaction was stirred for 4 hours. The solution was extracted twice with saturated aqueous sodium bicarbonate (500 mL). The organic phase was dried with MgSO4, filtered and the solvent removed under reduced pressure. The residue was chromatographed on silica gel packed in 98:2 CH2 Cl2 :MeOH and eluted with same. The appropriate fractions were combined and the solvent was removed under reduced pressure the give the desired 2,4-dimethyl-3-chloromethylpyridine-N-oxide. |
Here is a chemical reaction formula: Reactants are:m3_m4_m6:C(=O)(OC(C)(C)C)N[C@@H]1CC[C@H](CC1)O;m3_m4_m6:N(=NC(=O)OCC)C(=O)OCC;m1_m5_m2:OC1=CC(=C(C(=O)OC)C=C1)OC;m1_m5_m2:C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1, Reagents are:m3_m4_m6:C1CCOC1;m1_m5_m2:C1CCOC1, and Products are 0:C(=O)(OC(C)(C)C)N[C@@H]1CC[C@@H](CC1)C(=O)OC1=CC(=C(C(=O)OC)C=C1)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred solution of methyl 4-hydroxy-2-methoxybenzoate (1.09 g, 6.0 mmol) in dry THF (7 mL) was added triphenylphosphine (1.57 g, 6.0 mmol) and the solution was cooled to 0° C. A 4.0 mL volume of N-Boc-trans-1-amino-4-cyclohexanol (1 g, 4.0 mmol) and diethyl azodicarboxylate (945 μL, 6.0 mmol) in THF was added dropwise via addition funnel over 0.5 h. The reaction was filtered and the solvent was removed under reduced pressure. The residue was chromatographed on a silica gel column packed in 70:30 hexanes:EtOAc and eluted with same. The appropriate fractions were combined and the solvent removed under reduced pressure to afford methyl 4-[N-Boc-cis-1-amino-4-cyclohexanoyloxy]-2-methoxybenzoate. |
Here is a chemical reaction formula: Reactants are:m1_m4_m2_m3:C(=O)(OC(C)(C)C)N[C@@H]1CC[C@@H](CC1)C(=O)OC1=CC(=C(C(=O)OC)C=C1)OC;m1_m4_m2_m3:O;m1_m4_m2_m3:O[Li].O, Reagents are:m1_m4_m2_m3:C1CCOC1, and Products are 0:C(=O)(OC(C)(C)C)N[C@@H]1CC[C@@H](CC1)C(=O)OC1=CC(=C(C(=O)O)C=C1)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred solution of methyl 4-[N-Boc-cis-1-amino-4-cyclohexanoyloxy]-2-methoxybenzoate (220 mg, 0.52 mmol) in THF:H2O (5 mL: 1 mL) was added LiOH.H2O (67.6 mg, 1.59 mmol). The reaction was heated to 45° C. over 12 h and then cooled to ambient temperature. The solvent was removed under reduced pressure. The crude solid passed through a plug of silca gel packed in 50:50 MeOH:CH2Cl2 and eluted with same. The solvent was removed under reduced pressure to afford 4-[N-Boc-cis-1-amino-4-cyclohexanoyloxy]-2-methoxybenzoic acid as a white solid. |
Here is a chemical reaction formula: Reactants are:m2:[BH4-].[Na+];m1_m3:S(=O)(=O)=C1OC=CC(C1)=O, Reagents are:m1_m3:CO, and Products are 0:S(=O)(=O)=C1OC=CC(=C1)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A stirred solution of sulfonylpyran-4-one (1.2 g, 8.1 mmol) in MeOH (20 mL) was cooled to 0° C. under Argon and treated with NaBH4 (331 mg, 9.0 mmol). The reaction was stirred over 16 h and allowed to warm to ambient temperature. The solvent was removed under reduced pressure and the crude oil was chromatographed on a silica gel column packed in 50:50 EtOAc:hexanes and eluted with same. The appropriate fractions were combined and the solvent was removed under reduced pressure to give the sulfonylpyran-4-ol. |
Here is a chemical reaction formula: Reactants are:m1_m5_m2:OC1=CC(=C(C(=O)OC)C=C1)OC;m1_m5_m2:C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1;m1_m5_m2:C1CCOC1;m3_m4_m6:S(=O)(=O)=C1OC=CC(=C1)O;m3_m4_m6:N(=NC(=O)OCC)C(=O)OCC;m3_m4_m6:C1CCOC1, Reagents are:, and Products are 0:S(=O)(=O)=C1C=C(OC=C1)C(=O)OC1=CC(=C(C(=O)OC)C=C1)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred solution of methyl 4-hydroxy-2-methoxybenzoate (364 mg, 2.0 mmol) in dry THF (4 mL) was added triphenylphosphine (524.6 mg, 2.0 mmol) and the solution was cooled to 0° C. A 2.5 mL volume of sulfonylpyran-4-ol (200 mg, 1.33 mmol) and diethyl azodicarboxylate (315 μL, 2.0 mmol) in THF was added dropwise via addition funnel over 0.5 h. The reaction was filtered and the solvent was removed under reduced pressure. The residue was chromatographed on a silica gel column packed in 60:40 hexanes:EtOAc and eluted with same. The appropriate fractions were combined and the solvent removed under reduced pressure to afford methyl 4-[4-sulfonylpyranoyloxy]-2-methoxybenzoate. |
Here is a chemical reaction formula: Reactants are:m1_m4_m2_m3:S(=O)(=O)=C1C=C(OC=C1)C(=O)OC1=CC(=C(C(=O)OC)C=C1)OC;m1_m4_m2_m3:O;m1_m4_m2_m3:O[Li].O, Reagents are:m1_m4_m2_m3:C1CCOC1, and Products are 0:S(=O)(=O)=C1C=C(OC=C1)C(=O)OC1=CC(=C(C(=O)O)C=C1)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred solution of methyl 4-[4-sulfonylpyranoyloxy]-2-methoxybenzoate (470 mg, 1.5 mmol)in THF:H2O (18 mL: 2 mL) was added LiOH.H2O (128 mg, 3 mmol). The reaction was heated to 45° C. over 12 h and then cooled to ambient temperature. The solvent was removed under reduced pressure. The crude solid passed through a plug of silca gel packed in 80:20 hexanes:EtOAc and eluted with same. The solvent was removed under reduced pressure to afford 4-[4-sulfonylpyranoyloxy]-2-methoxybenzoic acid as a white solid. |
Here is a chemical reaction formula: Reactants are:m1_m4_m2_m3:S(=O)(=O)=C1CC(OC2=CC=CC=C12)C(=O)OC1=CC(=C(C(=O)OC)C=C1)OC;m1_m4_m2_m3:O;m1_m4_m2_m3:O[Li].O, Reagents are:m1_m4_m2_m3:C1CCOC1, and Products are 0:S(=O)(=O)=C1CC(OC2=CC=CC=C12)C(=O)OC1=CC(=C(C(=O)O)C=C1)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred solution of methyl 4-[4-sulfonylchromanoyloxy]-2-methoxybenzoate (500 mg, 1.38 mmol) in THF:H2O (18 mL: 2 mL) was added LiOH.H2O (175 mg, 4.14 mmol). The reaction was heated to 45° C. over 12 h and then cooled to ambient temperature. The solvent was removed under reduced pressure. The crude solid was passed through a plug of silca gel packed in 50:50 MeOH:CH2Cl2 and eluted with same. The solvent was removed under reduced pressure to afford 4-[4-sulfonylchromanoyloxy]-2-methoxybenzoic acid as a white solid. |
Here is a chemical reaction formula: Reactants are:m1_m5_m2:FC=1C(=CC(=C(C(=O)OC)C1)OC)O[C@@H](C)C1=CC=NC=C1;m1_m5_m2:[OH-].[Na+];m3:Cl;m4:O.CC#N, Reagents are:m1_m5_m2:CO, and Products are 0:FC=1C(=CC(=C(C(=O)O)C1)OC)O[C@@H](C)C1=CC=NC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred solution of methyl 5-fluoro-2-methoxy-4-[1-(S)-(4-pyridyl)ethoxy]benzoate (290 mg, 0.95 mmol) in methanol (5 mL) was added aqueous NaOH (396 μL, 3.6M). The reaction was stirred at ambient temperature overnight and then heated to 45° C. in an oil bath for another 24 h. The reaction pH was lowered to pH 3 using 1N HCl and the reaction mixture stripped down under reduced pressure. The white foam was lyophilized from H2O/CH3CN to afford the 5-fluoro-2-methoxy-4-[1-(S)-(4-pyridyl)ethoxy]benzoic acid as a white powder. |
Here is a chemical reaction formula: Reactants are:m3_m4:FC(CO)(F)F;m3_m4:C(C)N(CC)CC;m1_m5_m7_m2:FC(S(=O)(=O)Cl)(F)F;m1_m5_m7_m2:C(=O)=O, Reagents are:m6:CCOCC;m1_m5_m7_m2:C(Cl)Cl;m1_m5_m7_m2:CC(C)O, and Products are 0:FC(COS(=O)(=O)C(F)(F)F)(F)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of trifluoromethanesulfonyl chloride (640 μL, 6 mmol) in CH2Cl2 (5 mL) was cooled under argon to -78° C. (IPA:dry ice bath). 2,2,2-Trifluoroethanol was added (365 μL, 5 mmol) and triethylamine (834 μL, 6 mmol) was added dropwise. The reaction was stirred for 1.5 hours then warmed to 0° C. for 1 hour. Anhydrous ether (20 mL) was added and the mixture was stirred at 0° C. for 30 minutes. The solids were filtered off and the solvent was removed under reduced pressure with the flask maintained at 0° C. This afforded the 2,2,2-trifluoroethyltriflate as a yellow oil which was used immediately. |
Here is a chemical reaction formula: Reactants are:m3_m4:FC(CO)(F)F;m3_m4:C(C)N(CC)CC;m1_m5_m7_m2:FC(S(=O)(=O)Cl)(F)F;m1_m5_m7_m2:C(=O)=O, Reagents are:m6:CCOCC;m1_m5_m7_m2:C(Cl)Cl;m1_m5_m7_m2:CC(C)O, and Products are 0:FC(COS(=O)(=O)C(F)(F)F)(F)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of trifluoromethanesulfonyl chloride (800 uL, 7.5 mmole) in CH2Cl2 (6 mL) was cooled under argon to -60° C. (IPA:dry ice bath). 2,2,2-Trifluoroethanol was added (456 uL, 6 mmol) and triethylamine (1.04 uL, 7.5 mmol) was added dropwise. The reaction was stirred for 1.5 hours then warmed to 0° C. for 1 hour. Anhydrous ether (20 mL) was added and the mixture was stirred at 0° C. for 30 minutes. The solids were filtered off and the solvent was removed under reduced pressure with the flask maintained at 0° C. This afforded the 2,2,2-trifluoroethyltriflate as a yellow oil which was used immediately. |
Here is a chemical reaction formula: Reactants are:m3:Cl;m2:[OH-].[Na+];m1_m4_m5:COC1=C(C(=O)[O-])C=C(C(=C1)OCC(F)(F)F)F, Reagents are:m1_m4_m5:C1CCOC1;m1_m4_m5:O;m6:O, and Products are 0:FC(COC1=CC=C(C(=O)O)C=C1F)(F)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The above methoxy-4-trifluoroethoxy-5-fluorobenzoate (420 mg, 1.7 mmol) was dissolved in freshly distilled THF (50 mL) and water was added (20 mL) and 2N NaOH (2 mL) was dropped into the rapidly stirring solution at room temperature. The solution was warmed to 50° C. and stirred rapidly for 18 hours. The biphasic result was reduced to a smaller volume under reduced pressure and water was added to the aqueous residue to a volume of 50 mL and was then acidified with 4 N HCl to a pH of 1-2. The product was extracted with methylene chloride (3×50 mL). The combined organics were extracted with brine (50 mL) and the organic solvent was dried over MgSO4 and filtered and the solvent was removed under reduced pressure to give the desired 4-trifluoroethoxy-5-fluorobenzoic acid. |
Here is a chemical reaction formula: Reactants are:m3_m1:CN(C1=CC2=C(S1)C=C(C=C2)OC)C;m3_m1:O1CCCC1;m2:Cl, Reagents are:, and Products are 0:COC1=CC2=C(CC(=O)S2)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To tetrahydrofuran (200 mL) containing 2-dimethylamino-6-methoxybenzo-[b]-thiophene (cf. U.S. Pat. No. 5,420,349) (20.00 g, 96.5 mmol) was added 1N aqueous HCl (200 mL) and the resulting mixture was heated to reflux for 3 h. The mixture was cooled, the layers were separated, and the aqueous layer was extracted with dichloromethane (300 mL). The combined organic layers washed with water (250 mL), dried (MgSO4), filtered and concentrated to give crude product, which was recrystallized from 3A-ethanol, and dried in vacuo at room temperature to afford the title compound (13.89 g, 77.0 mmol, 80%): mp 80°-82° C.; IR (KBr) 1713, 1605, 1485, 1287, 1015, 865, 813 cm-1 ; 1H NMR (DMSO-d6) δ7.22 (d, 1H, J=8.4 Hz), 7.11 (s, 1H), 6.78 (d, 1H, J=8.4 Hz), 4.06 (s, 2H), 3.71 (s, 3H); 13 C NMR (DMSO-d6) δ203.5, 159.0, 136.9, 125.6, 124.6, 112.3, 108.4, 55.3, 46.2. Anal. Calcd. for C9H8O2S: C, 59.98; H, 4.47; S, 17.78. Found: C, 60.19; H, 4.57; S, 18.03. |
Here is a chemical reaction formula: Reactants are:m2:COC=1C=C(C(C=O)=CC1)O;m1_m3_m4:COC1=CC2=C(CC(=O)S2)C=C1, Reagents are:m5:C(C)N(CC)CC;m1_m3_m4:C(C)O;m1_m3_m4:C(Cl)Cl, and Products are 0:COC1=CC2=C(C3C(C(O2)=O)C2=C(S3)C=C(C=C2)OC)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred solution of 6-methoxythianaphthen-2-one (see Docket B-9459) (20 g, 111 mmol) in a mixture of ethanol (100 mL) and methylene chloride (50 mL) was added 4-methoxysalicylaldehyde (17.5 g, 115 mmol) followed by triethylamine (567 mg, 784 mL, 5.6 mmol) at room temperature. After 30 min, a solid began to precipitate and stirring was continued overnight. The mixture was then diluted with cold hexane (1 L) and filtered to yield 28.7 g (82%) of the title product as an off-white solid, pure by 1 H-NMR analysis. An analytical sample was obtained by recrystallization from toluene as light yellow crystals, mp 157-165 d°C.: 1 H-NMR (300 MHz, CDCl3) d 7.33 (d, J=8.6 Hz, 1H), 7.31 (d, J=8.1 Hz, 1H), 6.75 (d, J=2.4 Hz, 1H), 6.70 (m, 2H), 6.60 (d, J=2.5 Hz, 1H), 5.22 (d, J=7.2 Hz, 1H), 4.33 (d, J=7.2 Hz, 1H), 3.79 (s, 3H), 3.76 (s, 3H); IR (CHCl3) 1759 cm-1 ; MS (FD) m/e 314 (M+); Anal. calc'd. for C17H14O4S: C, 64.95; H, 4.50. Found: C, 65.01; H, 4.58. |
Here is a chemical reaction formula: Reactants are:m1_m6_m2_m3_m4_m5:FC(S(=O)(=O)OC1=CC2=C(C3=C(C(O2)C2=CC=C(C=C2)OCCN2CCCCC2)C2=C(S3)C=C(C=C2)OS(=O)(=O)C(F)(F)F)C=C1)(F)F;m1_m6_m2_m3_m4_m5:C1(=CC=CC=C1)P(C1=CC=CC=C1)CCC;m1_m6_m2_m3_m4_m5:C(=O)O;m1_m6_m2_m3_m4_m5:C(C)N(CC)CC, Reagents are:m1_m6_m2_m3_m4_m5:CN(C=O)C;m1_m6_m2_m3_m4_m5:C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-], and Products are 0:N1(CCCCC1)CCOC1=CC=C(C=C1)C1OC2=C(C3=C1C1=C(S3)C=CC=C1)C=CC=C2, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of the product of Example 6 (780 mg, 1.06 mmol), palladium(II) acetate (42 mg, 0.19 mmol), 1,2-bis(diphenylphosphinopropane (149 mg, 0.36 mmol), formic acid (0.6 mL), and triethylamine (3.0 mL) in anhydrous dimethylformamide (40 mL) was stirred at ambient temperature for 4 d. After concentration, the residue was subjected chromatography (silica gel, 1:1 hexane:ethylacetate, 2-10% methanol, 0.1% ammonium hydroxide). Product containing fractions were concentrated, partitioned between methylene chloride (100 mL) and saturated sodium bicarbonate (100 mL), and the aqueous layer extracted with methylene chloride (50 mL). The combined organic extracts were dried (sodium sulfate), concentrated, and the residue purified by chromatography (silica gel, 1:1 hexane:ethylacetate, 2-10% methanol, 0.1% ammonium hydroxide) to give 267 mg (57%) of the title compound as an oil which gave a white, crystalline solid, mp 107° C., upon trituration with ether/hexane: 1H NMR (300 MHz, CDCl3) d 7.86 (d, J=7.4 Hz, 1H), 7.40 (m, 1H), 7.1-7.3 (m, 6H), 6.97 (t, J=7.3 Hz, 1H), 6.89 (d, J=8.1 Hz, 1H), 6.84 (d, J=8.6 Hz, 2H), 6.66 (s, 1H), 4.07 (t, J=6.1 Hz, 2H), 2.75 (t, J=6.1 Hz, 2H), 2.49 (m, 4H), 1.5-1.7 (m, 4H), 1.4-1.5 (m, 2H); 13C NMR (125 MHz, CDCl3) d 159.1, 151.6, 139.3, 137.1, 133.0, 131.5, 129.8, 129.1, 126.8, 124.6, 124.4, 123.7, 122.6, 121.5, 121.5, 119.3, 116.9, 114.6, 77.6, 65.7, 57.7, 54.9, 25.8, 24.0; MS (FD+) m/e 441 (M+); Anal. calc'd for C28H27NO2 S: C, 76.15; H, 6.17; N, 3.17. Found: C, 75.93; H, 6.44; N, 3.01. |
Here is a chemical reaction formula: Reactants are:m1_m2_m5:C(=O)(OC)C1C(CCC2=CC(=CC=C12)OC)=O;m1_m2_m5:C1(O)=CC(O)=CC=C1;m3:P(=O)(Cl)(Cl)Cl;m4:O, Reagents are:m1_m2_m5:C1(=CC=CC=C1)C, and Products are 0:COC=1C=C2CCC=3C4=C(OC(C3C2=CC1)=O)C=C(C=C4)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 1-carbomethoxy-6-methoxy-2-tetralone (see, Colvin, Martin, and Shroot, Chemistry and Industry, 2130 (1966)) (18.0 g, 76.8 mmol) and resorcinol (8.9 g, 80.7 mmol) stirring at ambient temperature in toluene (450 mL) was added phosphorus oxychloride (12.0 g, 7.3 mL, 18.3 mmol) dropwise, and the mixture warmed to 80° C. for 12 h. After cooling to room temperature, the mixture was poured into water (500 mL) and filtered, rinsing the precipitate with ether. The filtrate layers were separated, the aqueous layer was extracted with ethyl acetate (3×500 mL), and the combined organic layers were dried (sodium sulfate) and concentrated. Recrystallization of the residue from methanol provided 16.0 g of the title compound as a yellow solid, mp 244-249 d°C.: 1 H NMR (300 MHz, DMSO-d6) d 10.55 (br s, 1H), 8.24 (d, J=8.6 Hz, 1H), 7.75 (d, J=8.7 Hz, 1H), 6.6-7.0 (m, 4H), 3.76 (s, 3H), 2.8-3.0 (m, 4H); 13C NMR (125 MHz, DMSO-d6) d 170.3, 160.3, 158.3, 158.1, 153.3, 147.7, 137.5, 127.4, 125.8, 122.5, 114.5, 112.6, 112.4, 110.9, 101.4, 54.6, 26.3, 22.7; IR (KBr) 3250, 1676, 1618 cm-1 ; MS (FD+) m/e 294 (M+); Anal. calc'd. for C18H14O4 : C, 73.45; H, 4.80. Found: C, 73.15; H, 4.86. |
Here is a chemical reaction formula: Reactants are:m1_m4_m2_m3:COC=1C=CC2=C(C=CC=3C4=CC=C(C=C4CN(C23)C2=CC=C(C=C2)OCCN2CCCCC2)OC)C1;m1_m4_m2_m3:C(C)S;m1_m4_m2_m3:[Cl-].[Al+3].[Cl-].[Cl-], Reagents are:m1_m4_m2_m3:C(Cl)Cl, and Products are 0:OC=1C=CC2=C(C=CC=3C4=CC=C(C=C4CN(C23)C2=CC=C(C=C2)OCCN2CCCCC2)O)C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of the product of Example 13 (195 mg, 0.39 mmol) in methylene chloride (25 mL) was treated with ethanethiol (200 mg, 220 mL, 3.2 mmol) and aluminum chloride (320 mg, 2.4 mmol). After stirring for 4 h at ambient temperature, the mixture was quenched carefully with THF (25 mL) and saturated sodium bicarbonate (25 mL). The layers were separated, the aqueous layer was extracted with THF (25 mL), and the combined organic layers were dried (sodium sulfate) and concentrated. The residue was purified by radial chromatography (silica gel, 1:1 hexane:ethyl acetate, 10-20% methanol, under an ammonia atmosphere) to provide 110 mg (60%) of the title compound as a tan foam. An analytical sample was crystallized from methanol as a light red solid: 1H NMR (300 MHz, dimethylformamide-d7) d 9.92 (br s, 1H), 9.74 (br s, 1H), 7.99 (d, J=8.8 Hz, 1H), 7.78 (d, J=8.5 Hz, 1H), 7.69 (d, J=9.0 Hz, 1H), 7.63 (d, J=8.7 Hz, 1H), 7.23 (d, J=2.0 Hz, 1H), 6.98 (dd, J=9.0, 2.1 Hz, 1H), 6.84 (dd, J=8.4, 2.1 Hz, 1H), 6.73 (m, 5H), 3.92 (t, J=5.9 Hz, 2H), 2.57 (t, J=5.9 Hz, 2H), 2.38 (m, 4H), 1.4-1.5 (m, 4H), 1.3-1.4 (m, 2H); IR (KBr) 3560, 3490 cm-1 ; MS (FD+) m/e 466 (M+); Anal. calc'd. for C30 H30N2O3.0.5H2O: C, 75.75; H, 6.58; N, 5.89. Found: C, 75.82; H, 6.76; N, 5.95. |
Here is a chemical reaction formula: Reactants are:m2:C(C=1C(O)=CC=CC1)=O;m1_m3_m4:COC1=CC2=C(CC(=O)S2)C=C1, Reagents are:m5:C(C)N(CC)CC;m1_m3_m4:C(C)O;m1_m3_m4:C(Cl)Cl, and Products are 0:COC1=CC2=C(C=C1)C1C(OC3=C(C1S2)C=CC=C3)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred solution of 6-methoxythianaphthen-2-one (52.6 g, 290 mmol) in a mixture of ethanol (260 mL) and methylene chloride (130 mL) was added triethylamine (2.0 mL, 14.8 mmol) followed by salicylaldehyde (32 mL, 300 mmol) at room temperature. After 1 h, a solid began to precipitate and stirring was continued for 3.5 h. The mixture was then diluted with cold hexane and filtered to yield 68.3 g (83%) of the title product as a powdery white solid, pure by 1H-NMR analysis: 1H NMR (300 MHz, CDCl3) δ7.45 (d, J=7.5 Hz, 1H), 7.33 (m, 2H), 7.17 (m, 1H), 7.07 (d, J=8.1 Hz, 1H), 6.77 (d, J=2.4 Hz, 1H), 6.69 (dd, J=2.4, 8.5 Hz, 1H), 5.25 (d, J=7.4 Hz, 1H), 4.37 (d, J=7.3 Hz, 1H), 3.77 (s, 3H); 13C NMR (75 MHz, CDCl3) δ166.4, 160.7, 150.8, 141.4, 130.1, 129.0, 127.7, 127.0, 124.9, 119.5, 117.2, 111.2, 108.3, 55.5, 50.6, 49.6; IR (CHCl3) 1766 cm-1 ; MS (FD) m/e 284 (M+); Anal. calc'd. for C16H12O3S: C, 67.59; H, 4.26. Found: C, 67.77; H, 4.24. |
Here is a chemical reaction formula: Reactants are:m1_m3_m2:COC=1C=CC2=C(CCC=3C4=CC=C(C=C4C(N(C23)C2=CC=C(C=C2)OCCN2CCCCC2)=O)OC)C1;m1_m3_m2:[H-].[Al+3].[Li+].[H-].[H-].[H-], Reagents are:m1_m3_m2:C1CCOC1, and Products are 0:COC=1C=CC2=C(CCC=3C4=CC=C(C=C4CN(C23)C2=CC=C(C=C2)OCCN2CCCCC2)OC)C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of the product of Example 12 (350 mg, 0.69 mmol) in THF (25 mL) was treated with lithium aluminum hydride (129 mg, 3.4 mmol) inducing a moderate exotherm. The mixture was allowed to return to room temperature and stirred for 2 h, then briefly warmed to reflux, cooled, and quenched with ethyl acetate (50 mL) followed by saturated ammonium chloride (50 mL). The aqueous layer was extracted with ethyl acetate (2×50 mL), and the combined organic layers were dried (sodium sulfate), concentrated; and purified via radial chromatography (silica gel, 1:1 hexane:ethyl acetate, 5% methanol, under an ammonia atmosphere) to provide 248 mg (64%) of the title compound as a yellow foam: 1H NMR (300 MHz, CDCl3) δ7.28 (d, J=8.5 Hz, 1H), 7.05 (d, J=8.5 Hz, 1H), 6.79 (m, 3H), 6.72 (d, J=2.6 Hz, 1H), 6.65 (d, 9.0 Hz, 2H), 6.58 (d, J=2.6 Hz, 1H), 6.52 (dd, J=8.6, 2.6 Hz, 1H), 4.65 (s, 2H), 3.94 (t, J=6.1 Hz, 2H), 3.74 (s, 3H), 3.74 (s, 3H), 2.96 (dd, J=8.3, 5.6, 2H), 2.81 (dd, J=8.3, 5.9 Hz, 2H), 2.66 (t, J=6.1 Hz, 2H), 2.43 (m, 4H), 1.5-1.6 (m, 4H), 1.3-1.5 (m, 2H); 13C NMR (75 MHz, CDCl3) δ158.5, 158.3, 153.3, 141.7, 138.4, 134.6, 132.3, 126.6, 126.2, 125.3, 122.9, 121.7, 120.5, 114.9, 113.4, 112.3, 111.2, 111.0, 65.8, 57.8, 55.6, 55.2, 55.1, 54.8, 29.0, 25.7, 24.0, 22.2; IR (CHCl3) 1610, 1506 cm-1 ; MS (FD) m/e 496 (M+); Anal. calc'd. for C32H36N2O3 : C, 77.37; H, 7.32; N, 5.64. Found: C, 77.25; H, 7.12; N, 5.75. |
Here is a chemical reaction formula: Reactants are:m1:N;m2:COC(CN=C=S)OC, Reagents are:m3:CO, and Products are 0:COC(CNC(=S)N)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Methanol (200 mL) was saturated with ammonia and stirred with isothiocyanatoacetaldehyde dimethyl acetal (5.0 g) for 2 h. The mixture was concentrated and the residue was chromatographed (silica gel, 5% methanol/dichloromethane) to give the title compound. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:C(C1=CC=CC=C1)OC(CNC)=O;m1_m2_m3:C1(CCC(=O)O1)=O, Reagents are:m1_m2_m3:C1(=CC=CC=C1)C, and Products are 0:C(C1=CC=CC=C1)OC(CN(C)C(CCC(=O)O)=O)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of sarcosine benzyl ester (3.0 g, 30.7 mmol) and succinic anhydride (5.5 g, 30.7 mmol) in toluene (75 mL) was heated to reflux for 3 h, cooled, filtered, and the filtrate was concentrated. The residue was taken up in 5% aqueous sodium carbonate and extracted with ethyl acetate. The aqueous phase was adjusted to pH 3 with concentrated hydrochloric using Congo Red paper and extracted with ethyl acetate. The organic phase was washed with water, dried (magnesium sulfate) and concentrated to yield the title compound (7.4 g, 67.5%): TLC Rf 0.48 (silica, 9:1:1 dichloromethane:methanol:formic acid). |
Here is a chemical reaction formula: Reactants are:m1_m2:N[C@@H](CC(OC1CCCCC1)=O)C(=O)O.OC1[C@@H](O)[C@@H](O)[C@H](OCC2=CC=C(C)C=C2)[C@H](O1)CO;m1_m2:CN(C)C=O;m3:ON1N=NC2=C1C=CC=C2;m5:C(C)N=C=NCCCN(C)C;m4:N(CC(=O)O)C(=O)OC(C)(C)C, Reagents are:, and Products are 0:N(CC(=O)N[C@@H](CC(OC1CCCCC1)=O)C(=O)O)C(=O)OC(C)(C)C.OC1[C@@H](O)[C@@H](O)[C@H](OCC2=CC=C(C)C=C2)[C@H](O1)CO, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a cold solution of Asp(O-cHex)-Man(4-MBzl) (46.7 g, 86.4 mmol) in DMF (100 mL) diisopropylethylamine (15 mL, 86.1 mmol) was added. N-Hydroxybezotriazole (14.0 g, 104 mmol) was added followed by Boc-Gly (16.6 g, 94.8 mmol). The reaction mixture was stirred in the cold for a few minutes, and N-ethyl-N'(dimethylaminopropyl)carbodiimide (18.2 g, 94.9 mmol) was added. The reaction mixture was allowed to warm to room temperature and stirred for 18 h. The reaction mixture was concentrated to a small volume and poured into 1.5 L of aqueous 10% K2CO3. The precipitated product was collected by filtration and was washed with water to a neutral pH to afford the titled compound (50.6 g). |
Here is a chemical reaction formula: Reactants are:m1_m3:[C@@H]1(C[C@H](O)[C@@H](CO)O1)N1C(=O)N=C(N)C=C1;m2:C(C)(=O)OC(C)=O, Reagents are:m1_m3:CN(C=O)C, and Products are 0:C(C)(=O)NC1=NC(N([C@H]2C[C@H](O)[C@@H](CO)O2)C=C1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To 61.29 g (270 mmol) of the material of Example I dissolved in 1300 ml of anhydrous N,N-dimethylformamide ("DMF") (Aldrich; Cat. No. 22, 70506), was added 28 ml (296 mmol) of acetic anhydride (Aldrich; Cat. No. 11,004-3), and the resulting mixture was stirred at room temperature for 20 hrs. DMF was removed under reduced pressure, and the resulting residue was treated with the excess of 100 ml dimethyl ether; 71.4 g (98% yield) of a crystalline product was obtained and collected by filtration, washed thoroughly with dimethyl ether, and dried over P2O5 for 3 hrs. This product had a melting point of 150°-170° C.; the published melting point for this product 154°-176° C. |
Here is a chemical reaction formula: Reactants are:m1:C([C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)O[C@H]([C@@H](CO)O)[C@@H]([C@H](CO)O)O)O)O)O)O.O;m2:C([C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)O[C@H]([C@@H](CO)O)[C@@H]([C@H](CO)O)O)O)O)O)O.O.O, Reagents are:, and Products are 0:C([C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)O[C@@H]2[C@H](O[C@@]([C@H]2O)(CO)O)CO)O)O)O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Examples XII-XXVII elucidate the conditions at which lactitol monohydrate and lactitol dihydrate, respectively, may be obtained from aqueous solutions of lactitol. In each instance 200 g lactitol dihydrate was used as the starting material which wasd dissolved in an amount of water varying from 40 g to 50 g at 100° C. Thereupon the solutions obtained were cooled to a temperature varying from 25° C. to 45° C. and seeded with 2 g monohydrate or 2 g dihydrate. The crystallization proper occurred at temperatures between 18° C. and 45° C. |
Here is a chemical reaction formula: Reactants are:m1_m2:N1=C(Cl)N=C(Cl)N=C1Cl;m1_m2:C1(=CC(=CC=C1)C)C, Reagents are:, and Products are 0:ClC1=NC(=NC(=N1)C1=C(C=C(C=C1)C)C)C1=C(C=C(C=C1)C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The reaction of cyanuric chloride with 1,3-xylene under Friedel-Crafts conditions to give 2-chloro-4,6-bis(2,4-dimethylphenyl)-s-triazine is known, e.g. from DE-A-1 169 947 and Helv. Chim. Acta 55, 1589 (1972). However, the product can also be obtained using an appropriate Grignard reagent, such as described in Helv. Chim. Acta 33, 1365 (1950) and U.S. Pat. No. 4,092,466. |
Here is a chemical reaction formula: Reactants are:m2:C(C)(=O)[O-].[Na+];m3:Cl.NO;m4:C1(CCCC2=CC=CC=C12)=O;m1:O, Reagents are:m6:C(C)O;m5:C(C)O, and Products are 0:C1(CCCC2=CC=CC=C12)=NO, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To 4.6 L of water at room temperature in a 4-neck 50 L flask sitting in a steam bath apparatus equipped with an overhead stirrer, a temperature probe and reflux condenser was added 3.72 Kg (27.36 mol) of sodium acetate with stirring, followed by 1.9 Kg of hydroxylamine hydrochloride (27.36 mol). To this slurry at room temperature, 12 L of ethanol was added followed by 1.994 Kg (13.68 mol) of 1-tetralone. Additional ethanol (1.7 L) was used to rinse off the funnel and added to the reaction mixture. The resulting light orange slurry was heated to 75° C. over 40 minutes and maintained at 75°-85° C. for another 75 minutes. The reaction mixture was cooled with the aid of ice packed around the flask. When the internal temperature reached 32° C., the reaction mixture was pumped over 15 minutes into 60 L of ice contained in a 200 L vessel. The reaction vessel was washed with an additional 2 L of water which was added to the 200 L vessel. When the ice melted, the mixture was filtered through a filter pad and the wet cake washed with 4 L of water. The wet cake was suction dried for 1 hour then transferred to two trays and dried under vacuum at 40° C. for 2 days to give 2.094 Kg (13.01 mol, 95%) of product. 1H NMR (250 MHz,CDCl3): 1.90 (m,2H), 2.80 (t,6 Hz,2H), 2.88 (t,6 Hz,2H), 7.15-7.35 (m,3H), 7.90 (d,8 Hz,1H), 8.9 (br s,1H). |
Here is a chemical reaction formula: Reactants are:m4:C1(CCCC2=CC=CC=C12)=NO;m1:CS(=O)(=O)O;m3:CS(=O)(=O)O;m5:[OH-].[Na+];m2:O=P12OP3(=O)OP(=O)(O1)OP(=O)(O2)O3, Reagents are:, and Products are 0:N1C(CCCC2=C1C=CC=C2)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To 10 L of methanesulfonic acid in a 22 L 3-neck flask equipped with an overhead stirrer, a temperature probe, nitrogen inlet and reflux condenser was added 2.6 Kg (18.61 mol) of phosphorus pentoxide. An additional 1.6 L of methanesulfonic acid was used to wash all the phosphorus pentoxide into the vessel. The mixture was heated at 90° C. for 2.5 hours then cooled to 50° C. using an ice bath and treated with 2.00 Kg (12.41 mol) of 1-tetralone oxime in several portions over 15 minutes. The mixture was heated at 63° C. for 10 minutes then slowly heated to 80° C. and kept at 80° C. for 3 hours, The reaction mixture was pumped into 70 L of ice then treated slowly with 11.25 L of 50% aqueous sodium hydroxide over 90 minutes at such a rate so as to maintain the temperature below 28° C. The mixture was filtered and 4 L of the filtrate was used to rinse the vessel. The wet cake (pink) was washed with 8 L of water then suction dried for 45 minutes then transferred to two trays and dried under vacuum at 40° C. for 2 days to give 1.9 Kg (11.79 mol, 95%) of product. 1H NMR (250 MHz,CDCl3): 2.24 (m,2H), 2.38 (t,6 Hz,2H), 2.82 (t,6 Hz,2H), 7.03 (d,8 Hz,1H), 7.13 (m,1H), 7.24 (m,2H), 8.63 (br s,1H). |
Here is a chemical reaction formula: Reactants are:m1:N1C(CCCC2=C1C=CC=C2)=O;m6_m2:C[Si](N[Si](C)(C)C)(C)C;m4_m5_m7:S(=O)([O-])[O-].[Na+].[Na+];m4_m5_m7:S(=O)([O-])[O-].[Na+].[Na+];m3:II, Reagents are:m6_m2:C(Cl)Cl;m4_m5_m7:O, and Products are 0:IC1C(NC2=C(CC1)C=CC=C2)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A suspension of 1.8 Kg (11.17 mol) of 2,3,4,5-tetrahydro-1H-1-benzazepin-2-one in a mixture of 22.33 L of methylene chloride and 11.78 L (55.83 mol) of hexamethyldisilazane was heated at reflux for 10 minutes then cooled to 30° C. and treated with 8.503 Kg (33.5 mol) of iodine in one portion. The mixture was heated at reflux for 2.5 hours then cooled to room temperature. Aqueous sodium sulfite containing 4.926 Kg of sodium sulfite in 44 L of water was cooled to 0° C. and into it was poured the reaction mixture in several portions with vigorous stirring while maintaining the temperature below 10° C. The reaction vessel was rinsed with 22.33 L of methylene chloride and the washing transferred to the quenching mixture. The quenching mixture was stirred vigorously and the layers allowed to separate. The aqueous layer was removed and reextracted with 22.33 L of methylene chloride. The combined organic layers were washed with 11 L of water and concentrated under vacuum to a final volume of approximately 5 L. The residue was treated with 55 L of toluene and concentrated under vacuum to a final volume of 10 L. The resulting slurry was removed by filtration and the filter cake washed with an additional 5 L of toluene and dried under vacuum at ambient temperature for 24 hours to give 1.842 Kg (6.42 mol, 57%) of product. 1H NMR (200 MHz,CDCl3): 2.6-2.8 (m,3H), 2.93 (m,1H), 4.64 (t,8 Hz,1H), 6.97 (d,8 Hz,1H), 7.10-7.35 (m,3H), 7.55 (br s,1H). |
Here is a chemical reaction formula: Reactants are:m1:C(C)(C)(C)OC(=O)N1C(CC1(C)C)=O;m2:[OH-].[Li+], Reagents are:m4_m5:CCOCC;m4_m5:O;m3:O1CCCC1, and Products are 0:C(C)(C)(C)OC(=O)NC(CC(=O)O)(C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A 3 L, 3-neck round bottom flask equipped with a magnetic stirrer, thermometer, nitrogen bubbler and addition funnel was charged with 180.3 g (0.89 mol) of N-(t-butoxycarbonyl)-4,4-dimethylazetidin-2-one dissolved in 1 L of tetrahydrofuran. The solution was cooled to 0°-5° C. and treated dropwise with 890 mL of 1.0M aqueous lithium hydroxide over 30 minutes. The reaction mixture was stirred at 0°-5° C. for 2 hours then diluted with 1 L of ether and 1 L of water. The layers were allowed to separate and the aqueous layer reextracted with an additional 1 L of ether. The aqueous layer was acidified by the addition of 1 L of saturated aqueous sodium bisulfate, then extracted with 1×1 L and 2×500 mL of ether. The combined organic layer and ether extracts were washed with 500 mL of saturated aqueous sodium chloride, dried over magnesium sulfate and concentrated under vacuum to 173 g of a yellow oil that solidified upon standing. The material was slurried with warm hexane then filtered and dried under high vacuum to afford 168.5 g (0.775 mol, 87%) of product as a white solid. 1H NMR (200 MHz,CDCl3): 1.39 (s,6H), 1.44 (s,9H), 2.72 (s,2H). FAB-MS: calculated for C10H19NO4 217; found 218 (M+H,54%). |
Here is a chemical reaction formula: Reactants are:m4:F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N(C)C)(N(C)C)N(C)C;m1_m5_m2_m3:N[C@H]1C(NC2=C(CC1)C=CC=C2)=O;m1_m5_m2_m3:C(C)(C)(C)OC(=O)NC(CC(=O)O)(C)C;m1_m5_m2_m3:C(C)N(CC)CC, Reagents are:m1_m5_m2_m3:C(Cl)Cl;m6:C(C)(=O)OCC, and Products are 0:C(C)(C)(C)OC(=O)NC(CC(=O)N[C@H]1C(NC2=C(CC1)C=CC=C2)=O)(C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 8.70 g (49.4 mmol) of 3(R)-amino-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one (Step E) in 100 mL of methylene chloride was treated with 10.73 g (49.4 mmol) of 3-t-butoxycarbonylamino-3-methylbutanoic acid (Step H) and 13.8 mL of triethylamine (10.0 g, 99 mmol, 2 eq.). The reaction flask was immersed in an ambient temperature water bath then 26 g of benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (59 mmol, 1.2 eq) was added all at once and the mixture stirred at room temperature for 2 hours. The reaction mixture was added to 300 mL of ethyl acetate and washed three times with 5% aqueous citric acid, twice with saturated aqueous sodium bicarbonate and once with saturated aqueous sodium chloride. The organic layer was removed, dried over magnesium sulfate, filtered and the filtrate concentrated under vacuum. The residue was purified by preparative high pressure liquid chromatography on silica, eluting with ethyl acetate/hexane (4:1), to afford 17.42 g (46.4 mmol, 94%) of the product as a white solid. 1H NMR (200 MHz,CDCl3): 1.37 (s,6H), 1.44 (s,9H), 1.95 (m,1H), 2.46 (d,15 Hz,1H), 2.59 (d,15 Hz,1H), 2.6-3.0, (m,3H), 4.53 (m,1H), 5.30 (br s,1H), 6.72 (d,7 Hz,1H), 6.98 (d,8 Hz,1H), 7.1-7.3 (m,3H), 7.82 (br s,1H). FAB-MS: calculated for C20H29N3O4 375; found 376 (M+H,70%). |
Here is a chemical reaction formula: Reactants are:m3_m6_m4:C1(=CC=CC=C1)C;m3_m6_m4:C=O;m1_m8_m2_m5:C[Mg]Cl;m1_m8_m2_m5:C1=CC(=CC=C1O)C, Reagents are:m3_m6_m4:CN1C(N(CCC1)C)=O;m7:O1CCCC1;m1_m8_m2_m5:O1CCCC1;m1_m8_m2_m5:O1CCCC1, and Products are 0:OC1=C(C=O)C=C(C=C1)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Methylmagnesium chloride solution in tetrahydrofuran (100 mL, 3.0M, 300 mmol) at room temperature was treated dropwise over 30 minutes with a solution of 32.3 g (300 mmol) of p-cresol in 30 mL of tetrahydrofuran. An additional 70 mL of tetrahydrofuran was added to moderate the exothermic reaction. The mixture was aged at room temperature for 2 hours then treated with 400 mL of toluene, 41mg of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone and 23 g of paraformaldehyde. The reaction mixture was heated at reflux for 18 hours, then cooled and washed with 200 mL of 2N aqueous hydrochloric acid and 200 mL of water. The organic layer was removed, filtered through Celite, dried over magnesium sulfate, filtered and solvents removed under vacuum. Crystallization of the crude residue from cold hexanes gave 7.4 g (54 mmol, 18%) of the product. The mother liquors were further purified by column chromatography on silica gel, eluting with methylene chloride, to give an additional 17.5 g (128 mmol, 43%) of the product. 1H NMR (200 MHz,CDCl3): 2.33 (s,3H), 6.89 (d,10 Hz,1H), 7.33 (m,2H), 9.83 (s,1H), 10.80 (s,1H). |
Here is a chemical reaction formula: Reactants are:m4_m7:BrCC=1C(=CC=CC1)C#N;m3_m6:OC1=C(C=O)C=C(C=C1)C;m5_m8:C[O-].[Na+];m1_m2:C[O-].[Na+];m1_m2:C(C)O, Reagents are:m9:O;m4_m7:CN(C=O)C;m3_m6:CN(C=O)C;m5_m8:CN(C=O)C, and Products are 0:C(#N)C1=C(C=CC=C1)C=1OC2=C(C1)C=C(C=C2)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A 500 mL 3-neck round bottom flask equipped with a magnetic stirrer, dropping funnel, thermometer and nitrogen bubbler was charged with 10.7 g (108 mmol) of sodium methoxide and 75 mL of absolute ethanol. A solution of 24.9 g (183 mmol) of 2-hydroxy-5-methylbenzaldehyde in 75 mL of dry dimethylformamide was added dropwise over 15 minutes. The mixture was stirred for 20 minutes then treated dropwise over 20 minutes with a solution of 34.8 g (177 mmol) of α-bromo-o-tolunitrile in 75 mL of dry dimethylformamide. The mixture was heated at 75° C. for 30 minutes, then allowed to cool for one hour. A suspension of 10.7 g (188 mmol) of sodium methoxide in 20 mL of dry dimethylformamide was added and the resulting mixture heated at 90° C. for 1.5 hours. The reaction mixture was concentrated under vacuum at 50° C. to give a brown solid that was slurried in 100-200 mL of cold water and filtered. The solids were triturated with 200 mL of methanol, filtered, washed with additional methanol, then air dried. After drying in a dessicator under high vacuum, 26.1 g (112 mmol, 63%) of the product was isolated as a beige solid. 1H NMR (200 MHz,CDCl3): 2.45 (s,3H), 7.17 (d,8 Hz,1H), 7.4 (m,3H), 7.6-7.8 (m,3H), 8.10 (d,8 Hz,1H). |
Here is a chemical reaction formula: Reactants are:m4:C[Sn](C)(C)N=[N+]=[N-];m1_m5_m2:C(#N)C1=C(C=CC=C1)C=1OC2=C(C1)C=C(C=C2)C;m1_m5_m2:C[Sn](C)(C)N=[N+]=[N-];m3:C[Sn](C)(C)N=[N+]=[N-], Reagents are:m1_m5_m2:C1(=CC=CC=C1)C, and Products are 0:N1N=NN=C1C1=C(C=CC=C1)C=1OC2=C(C1)C=C(C=C2)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A 500 mL 3-neck round bottom flask equipped with a magnetic stirrer, condenser, thermometer and nitrogen bubbler was charged with 19.1 g (82 mmol) of 2-(2-cyanophenyl)-5-methylbenzofuran, 200 mL of toluene and 25.6 g (124 mmol) of trimethyltin azide. The suspension was heated at reflux for 20 hours, then an additional 10.0 g (48 mmol) of trimethyltin azide was added and heating at reflux was continued for another 24 hours. Additional trimethyltin azide (5.8 g, 27 mmol) was added and refluxing continued for 5 hours. The reaction mixture was cooled to room temperature and solids were removed by filtration and washed with hexane and air dried. The solids were partitioned between 400 mL of 2N aqueous sodium hydroxide and 400 mL of ethyl acetate. The layers were separated and the aqueous layer was acidified by the addition of 2N hydrochloric acid, then extracted with 100 mL of ethyl acetate. The combined extracts were washed with saturated aqueous sodium chloride, dried over magnesium sulfate, filtered and refrigerated for 48 hours. The crystals that formed were removed by filtration, washed with hexane and air dried to give 12.97 g (47 mmol, 57%) of the product as fluffy, white crystals. 1H NMR (200 MHz,CDCl3): 2.38 (s,3H), 6.27 (s,1H), 7.05 (d,8 Hz,1H), 7.25 (m,2H), 7.4-7.7 (m,3H), 7.90 (d,8 Hz,1H). |
Here is a chemical reaction formula: Reactants are:m1_m2:N1N=NN=C1C1=C(C=CC=C1)C=1OC2=C(C1)C=C(C=C2)C;m1_m2:O1CCOCC1;m3_m5:BrBr;m4:C1=CCCCC1, Reagents are:m3_m5:C(Cl)(Cl)(Cl)Cl, and Products are 0:BrC1=C(OC2=C1C=C(C=C2)C)C2=C(C=CC=C2)C2=NN=NN2, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A 1 L 3-neck round bottom flask equipped with a magnetic stirrer, thermometer, dropping funnel and nitrogen bubbler was charged with 12.97 g (46.9 mmol) of 2-[2-(1H-tetrazol-5-yl)phenyl]-5-methylbenzofuran and 500 mL of 1,4-dioxane. To the well-stirred solution at room temperature was added a solution of 4.8 mL (93.2 mmol) of bromine in 35 mL of carbon tetrachloride dropwise over 1 hour. Cyclohexene (16 mL) was added to the reaction mixture then it was concentrated under vacuum to an oily residue that was partitioned between 100 mL of 1N aqueous sodium hydroxide and 100 mL of ether. The aqueous layer was removed, acidified with 50 mL of 2N aqueous hydrochloric acid, and extracted several times with ethyl acetate. The combined extracts were washed with saturated aqueous sodium chloride, dried over magnesium sulfate, filtered and concentrated under vacuum to give a white foam that was triturated with 100 mL of hot toluene. The mixture was cooled in an ice bath and the solids removed by filtration then washed with cold toluene, air dried and dried under vacuum to give 14.11 g (39.7 mmol, 85%) of product. 1H NMR (200 MHz,CDCl3 +1 drop DMSO-d6): 2.44 (s,3H), 7.1-7.3 (m,4H), 7.6 (m,2H), 7.86 (m,1H), 7.95 (m,1H). |
Here is a chemical reaction formula: Reactants are:m1_m0_m2:ClC1=C(C=C2C=C(C(=NC2=C1)C(=O)NCC(=O)O)O)OCC(F)(F)F, Reagents are:m1_m0_m2:C(=O)O, and Products are 0:Cl.OC=1C(=NC2=CC=C(C=C2C1)OCC(F)(F)F)C(=O)NCC(=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 0.5 g (1.3 mmol) of N-((7-chloro-3-hydroxy-6-(2,2,2-trifluoroethyloxy)quinolin-2-yl)carbonyl)glycine (title compound from Example 31) was dissolved in 26 ml of methanolic formic acid (4.4% strength), and a further 26 ml of methanolic formic acid were added at 20° C. After addition of 0.5 g of Pd/C (10%), the mixture was stirred at 20° C. for 1 hour, the catalyst was filtered off, the filtrate was concentrated and the residue was crystallized with diisopropyl ether. 250 mg of product were obtained, melting point>300° C. (sintering at 207° C.). |
Here is a chemical reaction formula: Reactants are:m4_m0:CCCCCCC.C(C)(=O)OCC;m1_m2_m3_m5:N1=C(C=CC2=CC=CC=C12)C(=O)O;m1_m2_m3_m5:S(=O)(=O)(O)C1=CC=C(C)C=C1.C(C1=CC=CC=C1)OC(CN)=O;m1_m2_m3_m5:C=1C=CC2=C(C1)N=NN2O, Reagents are:m1_m2_m3_m5:C(Cl)Cl, and Products are 0:C(C1=CC=CC=C1)OC=1C(=NC2=CC=C(C=C2C1)OC(C)C)C(=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 2.7 g (8 mmol) of the above quinolinecarboxylic acid were reacted with 2.7 g (8 mmol) of glycine benzyl ester tosylate, 4.4 ml (32 mmol) of NEM, 1.35 g (10 mmol) of HOBT and 3.6 g (8.8 mmol) of CMC in 300 ml of anhydrous methylene chloride at 20° C. for 24 hours, analogously to Example 25g). After working up and chromatography over silica gel with n-heptane/ethyl acetate (3:2), 3.5 g of oily product were obtained. |
Here is a chemical reaction formula: Reactants are:m0_m1:NCC(=O)N1[C@H](C(=O)N2[C@H](C(=O)O)C[C@@H](O)C2)CCC1;m3_m6:C(OCC1C2=CC=CC=C2C=2C=CC=CC12)(ON1C(CCC1=O)=O)=O;m2_m5:NCC(=O)N1[C@H](C(=O)N2[C@H](C(=O)O)C[C@@H](O)C2)CCC1;m4_m7:C(=O)([O-])[O-].[Na+].[Na+], Reagents are:m3_m6:C(OC)COC;m2_m5:C(=O)([O-])[O-].[Na+].[Na+].O;m4_m7:C(OC)COC, and Products are 0:N(CC(=O)N1[C@H](C(=O)N2[C@H](C(=O)O)C[C@@H](O)C2)CCC1)C(=O)OCC1C2=CC=CC=C2C2=CC=CC=C12, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Fmoc-Gly-Pro-Hyp was synthesized from Gly-Pro-Hyp as follows: 3.0 g Gly-Pro-Hyp (10.5 mmol) was dissolved in 54 mL Na2CO3 --H2O (1:9) and stored at 4° C. 4.05 g 9-fluorenylmethyl succinimidyl carbonate (12.0 mmol) was dissolved in 45 mL dimethoxyethane and stirred at 4° C. The aqueous Na2CO3 solution was added slowly to the dimethoxyethane solution, and the reaction proceeded for 2.5 h at 4° C. and 21 h at room temperature. The solution was filtered, and 360 mL H2O was added to the filtrate. The aqueous layer was extracted with 300 mL of diethyl ether, acidified to pH 2 with concentrated HCl, reduced to half volume at 80° C. under reduced pressure, and stored at 4° C. for 24 h. The aqueous layer was decanted from the oily precipitate, reduced to ~30 mL at 81° C. under reduced pressure, and stored at 4° C. for 24 h. The aqueous layer was decanted from the oily precipitate. Both oily precipitates were dissolved in a total of 20 mL methanol, then 250 mL ethyl acetate was added. A white residue was recovered by evaporation at 73° C. for 1 h under reduced pressure; yield 3.23 g (6.39 mmol, 60.6%). The identity of the product as Fmoc-Gly-Pro-Hyp and its homogeneity was verified by thin layer chromatography [chloroform-methanol-HOAc (95:20:3)], scanning UV spectroscopy, and Edman degradation sequence analysis. |
Here is a chemical reaction formula: Reactants are:m1_m4_m5_m2_m3:C(C1=CC=CC=C1)OC=1C(=NC(=CC1)CO)I;m1_m4_m5_m2_m3:C(C)(=O)[O-].[K+];m1_m4_m5_m2_m3:C(C=C)(=O)OCC, Reagents are:m1_m4_m5_m2_m3:CN(C)C=O;m1_m4_m5_m2_m3:O, and Products are 0:C(C1=CC=CC=C1)OC=1C(=NC(=CC1)CO)C(C(=O)OCC)=C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 3-benzyloxy-6-hydroxymethyl-2-iodopyridine (1.20 g, 3.50 mmol) in DMF (6.4 ml) and water (0.32 ml) were added potassium acetate (0.83 g, 8.5 mmol) palladium acetate (32 mg, 0.14 mmol) and ethyl acrylate (1.1 ml, 1.01 g, 10 mmol). The mixture was placed under nitrogen and stirred and heated at 120° C. for 1.25 h. By hplc the solution yield was 62%. |
Here is a chemical reaction formula: Reactants are:m1_m4_m5_m2_m6_m7_m3:BrC1=NC(=CC=C1OCC1=CC=CC=C1)CO;m1_m4_m5_m2_m6_m7_m3:C(C)(=O)[O-].[K+];m1_m4_m5_m2_m6_m7_m3:C(C=C)(=O)OC, Reagents are:m8:O;m1_m4_m5_m2_m6_m7_m3:CN(C)C=O;m1_m4_m5_m2_m6_m7_m3:O;m1_m4_m5_m2_m6_m7_m3:[I-].C(CCC)[N+](CCCC)(CCCC)CCCC;m1_m4_m5_m2_m6_m7_m3:Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl, and Products are 0:C(C1=CC=CC=C1)OC=1C(=NC(=CC1)CO)C(C(=O)OC)=C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 2-bromo-3-benzyloxy-6-hydroxymethylpyridine (2.94 g, 10 mmol) in DMF (19 ml) and water (1 ml) were added potassium acetate (2.45 g, 10.0 mmol), tetra-n-butylammonium iodide (3.69 g. 10.0 mmol), bis(triphenyl-phosphine)palladium dichloride (281 mg, 0.4 mmol) and methyl acrylate (2.70 ml. 2.58 g, 30 mmol). The mixture was placed under nitrogen and stirred and heated at 120° C. for 5 h. The mixture was cooled and added to water (180 ml). The product was extracted into ethyl acetate (3×30 ml). The combined extracts were washed with water (3×25 ml), dried and evaporated. The residue was purified by flash column chromatography eluting with dichloromethane, then 4:1 dichloromethane:ethyl acetate to give the product (2.516 g, 84%). |
Here is a chemical reaction formula: Reactants are:m1_m2_m8_m9:[H-].[Na+];m1_m2_m8_m9:C(C)(C)(C)OC(=O)NCC\C=C\C=1C=NC=NC1;m4_m5:IC;m3:C(C)(C)NC(C)C, Reagents are:m1_m2_m8_m9:COCCOC;m1_m2_m8_m9:CN(C)C=O;m4_m5:COCCOC;m6:O;m7:O, and Products are 0:CN(CC\C=C\C=1C=NC=NC1)C(=O)OC(C)(C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Under a nitrogen atmosphere, sodium hydride (0.78 g, 19.5 mmol, 60% dispersion in oil) was added to a stirring solution of IV (0.50 g, 2.0 mmol), 1,2-dimethyoxyethane (20 mL), DMF (25 mL), and a trace of diisopropylamine. The mixture was stirred at ambient temperature for 45 min, and a solution of iodomethane (2.59 g, 18.3 mmol) in 1,2-dimethoxyethane (5 mL) was added. The mixture was stirred at ambient temperature for 3 days, cooled, and water (25 mL) was added dropwise. The mixture was diluted with water (200 mL) and extracted with chloroform (7×50 mL). All chloroform extracts were combined, dried (Na2 SO4), filtered, and concentrated by rotary evaporation. The residue was dried under high vacuum at ambient temperature to give a red-brown oil. The oil was chromatographed on silica gel (50 g), eluting with ethyl acetate. Selected fractions were combined, concentrated by rotary evaporation, and dried under high vacuum at ambient temperature to give compound V as a light yellow oil (0.40 g, 76.1%). |
Here is a chemical reaction formula: Reactants are:m1_m2_m4:BrC(Br)(Br)Br;m1_m2_m4:C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1;m3:N1=CC(=CC=C1)C=O, Reagents are:m1_m2_m4:C(Cl)Cl, and Products are 0:BrC(=CC=1C=NC=CC1)Br, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Tetrabromomethane (24.82 g, 0.747 mole) and triphenylphosphine (39.17 g, 0.149 mole) were stirred together in dry methylene chloride (100 mL) for 5 min. at 0° C. under a nitrogen atmosphere. To this mixture was added dropwise pyridine 3-carboxaldehyde (4 g, 0.0373 mole). The solution was then stirred for 45 min. at ambient temperature. The reaction mixture was extracted with aqueous 6N hydrochloric acid (3×25 mL), the aqueous layer basified with solid sodium bicarbonate to pH 8-9 and extracted with chloroform (4×25 mL). The combined organic liquours were dried over anhydrous sodium sulfate, filtered and concentrated on a rotary evaporator to give a dark colored syrup. The crude product was chromatographed on silica gel (70-230 mesh) with chloroform:methanol (95:5) as eluant, to afford a light yellow solid (5.0 g, 70%) which rapidly turned dark on standing. |
Here is a chemical reaction formula: Reactants are:m3:[OH-].[Na+];m1_m2_m4:CC1=NC=C(C=C1)C2CCCN2;m1_m2_m4:C=O, Reagents are:m1_m2_m4:C(=O)O, and Products are 0:CC1=NC=C(C=C1)C2CCCN2C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Into a round bottom flask was placed XVI (2.0 g), and formaldehyde (37% w/v in water, 20 mL) and formic acid (95-97% w/v, 45 mL), both a 0° C., were added. The mixture then was refluxed under nitrogen for 8 hr. The cooled reaction mixture was basified with aqueous sodium hydroxide (50% w/v) to pH 8-9, and the solution extracted with chloroform (5×25 mL). The combined organic liquors were dried over anhydrous sodium sulfate, filtered and evaporated; and the resulting oil distilled under reduced pressure to afford XVII as a clear odorless oil (b.p. 107° C. at 3 mm Hg, 92% yield). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:C(C)(C)(C)OC(=O)N[C@H]([C@H](C(=O)OC)O)C1=CC=CC=C1;m1_m2_m3_m4:O=CC(Cl)(Cl)Cl;m1_m2_m3_m4:C1(=CC=C(C=C1)S(=O)(=O)[O-])C.[NH+]1=CC=CC=C1, Reagents are:m1_m2_m3_m4:C1(=CC=CC=C1)C, and Products are 0:COC(=O)[C@H]1[C@@H](NC(O1)C(Cl)(Cl)Cl)C1=CC=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 3.0 g of methyl (2R,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropionate, of 5 cm3 of chloral and of 0.05 g of pyridinium p-toluenesulphonate in 40 cm3 of anhydrous toluene is heated at reflux with distillation of the solvent. 15 cm3 of solvent are distilled and then 5 cm3 of chloral and 0.05 g of pyridinium p-toluenesulphonate are added. 20 cm3 of solvent are distilled and then 5 cm3 of chloral as well as 30 cm3 of anhydrous toluene are added. 25 cm3 of solvent are distilled and 5 cm3 of chloral and 35 cm3 of anhydrous toluene are added. 25 cm3 of solvent are distilled and then the solution is cooled to a temperature in the region of 20° C. The organic solution is washed with water (2 times 50 cm3), dried over sodium sulphate and concentrated to dryness under reduced pressure at approximately 50° C. The residue obtained is purified by liquid chromatography on silica gel, the eluent being an ethyl acetate/cyclohexane (1/3 by volume) mixture. There are thus obtained, with a yield of 91%, 3.0 g of (4S,5R)-5-methoxycarbonyl-4-phenyl-2-trichloromethyl-1,3-oxazolidine whose characteristics are the following: |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:BrCC(=O)OCC;m1_m2_m3:CSC, Reagents are:m1_m2_m3:CC(=O)C, and Products are 0:[Br-].C(=O)(OCC)C[S+](C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of ethyl bromoacetate (265 g) and dimethyl sulfide (114 g) in acetone (500 mL) was stirred at room temperature. After three days, the title compound was isolated by filtration of the reaction mixture. Melting point 88°-90° C. |
Here is a chemical reaction formula: Reactants are:m1_m5:[Br-].C(=O)(OCC)C[S+](C)C;m3:C1(C=CCC1)=O;m2:N12CCCCCC2=NCCC1;m4:Cl.[Cl-].[Na+], Reagents are:m1_m5:C1(=CC=CC=C1)C, and Products are 0:O=C1C2C(C2CC1)C(=O)OCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A suspension of carboethoxymethyl dimethylsulfonium bromide (45.5 g) in toluene (350 mL) was treated with 1,8-diazabicyclo[5.4.0]undec-7-ene (30.2 g). The resulting mixture was stirred at room temperature. After one hour, the reaction mixture was treated with 2-cyclopenten-1-one (19.57 g). After an additional 18 hours, the reaction mixture was added to a 1N hydrochloric acid/sodium chloride solution. The resulting mixture was extracted with diethyl ether. The combined ether extracts were dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified using silica-gel chromatography, eluting with a linear gradient of 10% ethyl acetate/hexanes to 50% ethyl acetate/hexanes, to give 22.81 g of the title compound. Melting point: 36°-38° C. |
Here is a chemical reaction formula: Reactants are:m1_m3:O=C1C2C(C2CC1)C(=O)OCC;m2:Cl, Reagents are:m1_m3:[OH-].[Na+], and Products are 0:O=C1C2C(C2CC1)C(=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 60 g of ethyl 2-oxobicyclo[3.1.0]hexane-6-carboxylate and 300 ml of 1N sodium hydroxide was stirred at 25°-30° C. After 2.5 hours, concentrated hydrochloric acid was added to adjust the pH to 0.8-1.2. The resulting solution was extracted with ethyl acetate. The extracts were dried over magnesium sulfate, filtered, and concentrated to give 49.1 g (98%) of the crude material. Recrystallization from 100 ml of ethyl acetate gave the title compound, mp 123.5°-128° C. |
Here is a chemical reaction formula: Reactants are:m1_m2_m4:OC1=C2C(C(N(C2=CC=C1)C)=O)C;m1_m2_m4:C([O-])([O-])=O.[K+].[K+];m3:COS(=O)(=O)OC, Reagents are:m1_m2_m4:CC(=O)C, and Products are 0:COC1=C2C(C(N(C2=CC=C1)C)=O)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A slurry of 1,3-dihydro-4-hydroxy-1,3-dimethyl-2H-indol-2-one (50 g), milled potassium carbonate (60.1 g) and HPLC grade acetone (400 ml) was mechanically stirred at room temperature as dimethylsulfate (41.4 ml) was added dropwise. The addition funnel was replaced with a condenser and the slurry was refluxed for 18 hours. The K2CO3 was filtered off and washed well with acetone. Acetone was evaporated and the residue was purified by column chromatography to yield 46.5 g of an oil. The oil was dissolved in ether and placed in the refrigerator where, upon standing overnight, the product crystallized, m.p. 73°-74° C. |
Here is a chemical reaction formula: Reactants are:m3:CC(C1=CC=CC=C1)N=C=O;m2:C1CCC2=NCCCN2CC1;m1_m4:CN1CC[C@@]2([C@H]1N(C=1C=CC=C(C21)O)C)C, Reagents are:m1_m4:C1CCOC1, and Products are 0:C[C@H](C1=CC=CC=C1)NC(OC1=C2[C@@]3([C@H](N(C2=CC=C1)C)N(CC3)C)C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: cis-(±)-1,2,3,3a,8,8a-Hexahydro-1,3a,8-trimethylpyrrolo [2,3-b]indol-4-ol (2g) was dissolved in degassed THF (200 ml). DBU (0.8 ml) was added to the mixture followed by R-(+)-α-methylbenzyl isocyanate (2 g). The reaction was stirred at room temperature overnight under nitrogen. The solvent was evaporated under reduced pressure and the residue was purified using Prep 500 chromatography (4% MeOH/DCM) to yield 1.2 g of a solid. This material was combined with 600 mg of identically prepared material, which was found to be pure by thin layer analysis. The combined product was triturated with isopropyl ether and filtered to yield 1.8 g of (±)-(3aR*, 8aS*)-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo [2,3-b]indol-4-yl (R)-(α-methylbenzyl)carbamate, m.p. 151°-155° C. |
Here is a chemical reaction formula: Reactants are:m2_m3:C(C(C)(C)C)(=O)OCCl;m2_m3:C(C(C)C)N(CC(C)C)CC;m5_m1:ClC=1C=CC2=C([C@H](O[C@@H](C(N2CC(C)C)=O)CC(=O)O)C2=C(C=CC=C2)Cl)C1;m4_m6:O, Reagents are:m5_m1:CN(C=O)C;m4_m6:C(C)(=O)OCC, and Products are 0:C(C(C)(C)C)(=O)OCOC(C[C@@H]1C(N(C2=C([C@H](O1)C1=C(C=CC=C1)Cl)C=C(C=C2)Cl)CC(C)C)=O)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: In N,N-dimethylformamide (10 ml) was dissolved trans- 7-chloro-5-(2-chlorophenyl)-1-isobutyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetic acid (0.5 g) obtained in Example 2. To the solution were added pivaloyloxymethyl chloride (0.43 ml), N,N-diisobutyl ethylamine (0.52 ml) and KI (0.2 g). The mixture was stirred at room temperature overnight. To the reaction mixture were added water (100 ml) and ethyl acetate (100 ml), followed by extraction. The ethyl acetate layer was washed with an aqueous solution of potassium hydrogensulfate, an aqueous solution of sodium hydrogencarbonate and water, successively, which was dried over anhydrous magnesium sulfate. The solvent was then distilled off under reduced pressure. The residue was purified by means of a silica gel column chromatography (hexane:ethyl acetate=10:1 to 5:1) to afford trans-7-chloro-5-(2-chlorophenyl)-1-isobutyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetic acid pivaloyloxymethyl ester (0.55 g). |
Here is a chemical reaction formula: Reactants are:m3:[BH4-].[Na+];m1_m2_m5:NC1=C(C(C2=C(C=CC=C2)Cl)O)C=C(C=C1)Cl;m1_m2_m5:COC1=C(C=O)C=CC(=C1)OC;m4:O, Reagents are:m1_m2_m5:C(C)(=O)O, and Products are 0:ClC=1C=CC(=C(C(C2=C(C=CC=C2)Cl)O)C1)NCC1=C(C=C(C=C1)OC)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 2-amino-5-chloro-α-(2-chloro phenyl)benzyl alcohol (5.0 g) and 2,4-dimethoxy benzaldehyde (3.72 g) in acetic acid (50 ml) was added, under ice-cooling, sodium borohydride (0.94 g). The mixture was stirred for one hour at room temperature, which was poured into water (200 ml), followed by extraction with ethyl acetate (200 ml×2). The ethyl acetate layer was washed with 1N sodium hydroxide, which was dried over anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The residue was purified by means of a silica gel column chromatography (hexane:ethyl acetate=5:1) to give 5-chloro-α-(2-chlorophenyl)-2-(2,4-dimethoxybenzyl)aminobenzyl alcohol (7.5 g) as an oily product. |
Here is a chemical reaction formula: Reactants are:m1_m2:O=C1CCC(O1)C(=O)O;m1_m2:S(=O)(Cl)Cl, Reagents are:, and Products are 0:O=C1CCC(O1)C(=O)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 4.9 g of 5-oxotetrahydrofuran-2-carboxylic acid and 5.5 ml of thionyl chloride was subjected to reflux for 2 hours. Thionyl chloride was then distilled off under reduced pressure to leave 5-oxotetrahydrofuran-2-carbonyl chloride. This product was mixed with 5.0 g of 2-aminobenzophenone, 200 ml of ethyl acetate and 200 ml of a saturated aqueous solution of sodium hydrogencarbonate, which was stirred for one hour at room temperature. The ethyl acetate layer was washed with water and dried over anhydrous magnesium sulfate, then the solvent was distilled off under reduced pressure. The residue was purified by means of a silica gel column chromatography (eluent, hexane:ethyl acetate=2:1) to give 2-(5-oxotetrahydrofuran-2-carbonyl)aminobenzophenone (6.5 g) as needles, m.p. 100° C.-102° C. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:ClC(C(=O)O)CC(C)C(=O)OC;m1_m2_m3:S(=O)(Cl)Cl, Reagents are:m1_m2_m3:C1(=CC=CC=C1)C, and Products are 0:ClC(C(=O)Cl)CCC(=O)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 7.6 g of 2-chloro-4-methoxycarbonyl valeric acid, 9.2 ml of thionyl chloride and 30 ml of toluene was stirred for 30 minutes at 80° C., followed by distilling off the solvent under reduced pressure to leave 2-chloro-4-methoxycarbonyl butyryl chloride. A mixture of this compound, 5.0 g of 2-benzylaminobenzophenone, 100 ml of ethyl acetate and 100 ml of a saturated aqueous solution of sodium hydrogencarbonate was stirred for 30 minutes at room temperature. The ethyl acetate layer was washed with water and dried over anhydrous magnesium sulfate, then the solvent was distilled off under reduced pressure. The residue was purified by means of a silica gel column chromatography (eluent, hexane:ethyl acetate=5:1) to give 1.2 g of 2-[N-benzyl-N-(2-chloro-4-methoxycarbonyl)butyryl]aminobenzophenone as an oily product. |
Here is a chemical reaction formula: Reactants are:m1_m2:ClC(C(=O)O)CC(C)C(=O)OC;m1_m2:S(=O)(Cl)Cl, Reagents are:, and Products are 0:ClC(C(=O)Cl)CCC(=O)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 6.2 g of 2-chloro-4-methoxycarbonyl valeric acid and 12.6 ml of thionyl chloride was refluxed for 30 minutes, then the solvent was distilled off under reduced pressure to leave 2-chloro-4-methoxycarbonyl butyryl chloride. A mixture of this product, 5.0 g of 2-benzylaminodiphenyl methanol, 100 ml of ethyl acetate and 100 ml of a saturated aqueous solution of sodium hydrogencarbonate was stirred for one hour at room temperature. The ethyl acetate layer was washed with water and dried over anhydrous magnesium sulfate. then the solvent was distilled off under reduced pressure. The residue was purified by means of a silica gel column chromatography (eluent, hexane:ethyl acetate=2:1) to give 5.3 g of 2-[N-benzyl-N-(2-chloro-4-methoxycarbonyl)butyryl]aminodiphenyl methanol as an oily product. |
Here is a chemical reaction formula: Reactants are:m3_m1:C(C1=CC=CC=C1)N1C([C@H](O[C@@H](C2=C1C=CC(=C2)Cl)C2=C(C=CC=C2)Cl)CO)=O;m2:CC(=O)C.OS(=O)(=O)O.O=[Cr](=O)=O, Reagents are:m3_m1:CC(=O)C, and Products are 0:C(C1=CC=CC=C1)N1C([C@H](O[C@@H](C2=C1C=CC(=C2)Cl)C2=C(C=CC=C2)Cl)C(=O)O)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: In 20 ml of acetone was dissolved 0.5 g of trans-1-benzyl-7-chloro-5-(2-chlorophenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-methanol obtained in Example 46. To the solution was added dropwise, while stirring at room temperature, 0.5 ml of a Jones reagent. The reaction mixture was stirred for one hour at room temperature, which was then concentrated under reduced pressure The concentrate was subjected to extraction with ethyl acetate. The organic layer was washed with water and dried, then the solvent was distilled off under reduced pressure. From the residue was obtained 0.23 g of trans-1-benzyl-7-chloro-5-(2-chlorophenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-carboxylic acid as white crystals, m.p.177°-178 C. |
Here is a chemical reaction formula: Reactants are:m1:C(C)OC(CNC(C[C@@H]1C(N(C2=C([C@@H](O1)C1=CC=CC=C1)C=C(C=C2)Cl)C(C)C)=O)=O)=O;m3:Cl;m2:C([O-])([O-])=O.[K+].[K+], Reagents are:m4_m5:CO;m4_m5:O, and Products are 0:ClC=1C=CC2=C([C@@H](O[C@@H](C(N2C(C)C)=O)CC(=O)NCC(=O)O)C2=CC=CC=C2)C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: In a mixture of 2 ml of methanol and 1 ml of water was suspended 48 mg of N-(trans-7-chloro-1-isopropyl-5-phenyl-1,2,3,5-tetrahydro-2-oxo-4,1-benzoxazepin-3-ylacetyl)glycine ethyl ester obtained in Example 55. To the suspension was added 0.1 g of potassium carbonate. The mixture was stirred for 6 hours at room temperature. The reaction mixture was adjusted to pH 4 with dilute hydrochloric acid, which was subjected to extraction with ethyl acetate. The organic layer was washed with water and dried, then the solvent was distilled off under reduced pressure. Crystals obtained form the residue were recrystallized from ether and hexane to afford 29 mg of N-(cis-7-chloro-1-isopropyl-5-phenyl-1,2,3,5-tetrahydro-2-oxo-4,1-benzoxazepin-3-ylacetyl)glycine as white needles. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:C(C)(=O)NC1=C(C(=O)C2=C(C=C(C=C2OC)OC)OC)C=C(C=C1)Cl;m1_m2_m3:Cl, Reagents are:m1_m2_m3:C(C)O, and Products are 0:NC1=C(C(=O)C2=C(C=C(C=C2OC)OC)OC)C=C(C=C1)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 4.7 g of 2-acetylamino-5-chloro-2',4',6'-trimethoxybenzophenone, 50 ml of 6N hydrochloric acid and 50 ml of ethanol was refluxed for 1 hour while heating. After the solvent was distilled off, the residue was basefied with an aqueous solution of sodium hydrogen carbonate and then extracted with ethyl acetate. After the extract was washed with water and dried, the solvent was removed, and the residue was subjected to silica gel column chromatography to yield 3.75 g of a crystal. |
Here is a chemical reaction formula: Reactants are:m3:O;m1_m4_m2:NC1=C(C(=O)C2=C(C=C(C=C2OC)OC)OC)C=C(C=C1)Cl;m1_m4_m2:[H-].[Al+3].[Li+].[H-].[H-].[H-], Reagents are:m1_m4_m2:O1CCCC1, and Products are 0:NC1=C(C(C2=C(C=C(C=C2OC)OC)OC)O)C=C(C=C1)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 3.0 g of 2-amino-5-chloro-2',4',6'-trimethoxybenzophenone in 50 ml of tetrahydrofuran, 0.43 g of lithium aluminum hydride was added, followed by stirring for 1 hour. After water was added, the solution was extracted with ethyl acetate and dried over anhydrous sodium sulfate, after which the solvent was removed and the residue was subjected to silica gel column chromatography to yield 2.9 g of a crystal. |
Here is a chemical reaction formula: Reactants are:m4:C(#N)[BH3-].[Na+];m1_m2_m3_m5:NC1=C(C(C2=C(C=C(C=C2OC)OC)OC)O)C=C(C=C1)Cl;m1_m2_m3_m5:CC(C=O)(C)C;m1_m2_m3_m5:C(C)(=O)O, Reagents are:m1_m2_m3_m5:C(C)O, and Products are 0:ClC=1C=CC(=C(C(C2=C(C=C(C=C2OC)OC)OC)O)C1)NCC(C)(C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: After a solution of 2.5 g of 2-amino-5-chloro-α-(2,4,6-trimethoxyphenyl)benzyl alcohol, 1.01 ml of trimethylacetaldehyde and 0.56 g of acetic acid in 30 ml of ethanol was stirred at room temperature for 1.5 hours, 0.81 g of sodium cyanoborohydride was added, followed by stirring overnight. After concentration and subsequent dilution with water, the solution was extracted with ethyl acetate. After solvent removal, the residue was subjected to silica gel column chromatography to yield 2.2 g of a crystal. |
Here is a chemical reaction formula: Reactants are:m1_m2_m5_m3_m4:ClC=1C=CC2=C([C@H](O[C@@H](C(N2CC(C)C)=O)CC(=O)O)C2=C(C=CC=C2)Cl)C1;m1_m2_m5_m3_m4:[Cl-].[NH4+];m1_m2_m5_m3_m4:Cl.C(C)N=C=NCCCN(C)C;m1_m2_m5_m3_m4:C(C)N(CC)CC, Reagents are:m6:O;m1_m2_m5_m3_m4:CN(C=O)C, and Products are 0:ClC=1C=CC2=C([C@H](O[C@@H](C(N2CC(C)C)=O)CC(=O)N)C2=C(C=CC=C2)Cl)C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1.0 g of trans-7-chloro-5-(2-chlorophenyl)-1-isobutyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetic acid and 0.5 g of ammonium chloride were dissolved in 8 mi of dimethylformamide, and 0.46 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and 0.7 ml of triethylamine were added, followed by stirring at room temperature for 30 minutes. After water was added, the solution was extracted with ethyl acetate, followed by washing with water, after which the solvent was removed and the residue was recrystallized to yield 0.75 g of a crystal. |
Here is a chemical reaction formula: Reactants are:m3:C(O)([O-])=O.[Na+];m1_m4_m2_m5:NC1=C(C(C2=C(C=CC=C2)Cl)O)C=C(C=C1)Cl;m1_m4_m2_m5:FC(C(=O)O)(F)F, Reagents are:m1_m4_m2_m5:ClCCl;m1_m4_m2_m5:ClCCl, and Products are 0:ClC=1C=CC(=C(C(C2=C(C=CC=C2)Cl)O)C1)NC(C(F)(F)F)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 1.0 g of 2-amino-5-chloro-α-(2-chlorophenyl)benzyl alcohol in 12 ml of dichloromethane, a solution of 0.8 g of anhydrous trifluoroacetic acid in 2 ml of dichloromethane was added. After reaction, an aqueous solution of sodium hydrogen carbonate was added, and the organic layer was dried, after which the solvent was removed and the residue was recrystallized from hexane to yield 1.3 g of a crystal. |
Here is a chemical reaction formula: Reactants are:m1_m4:[H-].[Al+3].[Li+].[H-].[H-].[H-];m2_m5:ClC=1C=CC(=C(C(C2=C(C=CC=C2)Cl)O)C1)NC(C(F)(F)F)=O;m3:O, Reagents are:m1_m4:C(C)OCC;m2_m5:O1CCCC1, and Products are 0:ClC=1C=CC(=C(C(C2=C(C=CC=C2)Cl)O)C1)NCC(F)(F)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a suspension of 0.25 g of lithium aluminum hydride in 20 ml of absolute ethyl ether, a solution of 1.2 g of 5-chloro-α-(2-chlorophenyl)-2-(trifluoroacetylamino)benzyl alcohol in 5 ml of tetrahydrofuran was added dropwise. After mixture stirring at room temperature for 1 hour, water was added, and the organic layer was dried, after which the solvent was removed and the residue was subjected to silica gel column chromatography to yield 1.0 g of an oily compound. |
Here is a chemical reaction formula: Reactants are:m1_m2_m4:ClC=1C=CC2=C([C@H](O[C@@H](C(N2CC(C)(C)C)=O)CC(=O)NC2=CC(=CC=C2)C#N)C2=C(C=CC=C2)Cl)C1;m1_m2_m4:[N-]=[N+]=[N-].[Na+];m3:O, Reagents are:m1_m2_m4:CN(C=O)C, and Products are 0:ClC=1C=CC2=C([C@H](O[C@@H](C(N2CC(C)(C)C)=O)CC(=O)NC2=CC(=CC=C2)C2=NN=NN2)C2=C(C=CC=C2)Cl)C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 0.2 g of trans-7-chloro-5-(2-chlorophenyl)-3-(3-cyanophenylaminocarbonylmethyl)-1-neopentyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine and 80 mg of sodium azide in 5 ml of dimethylformamide was stirred at 90° C. for 60 hours. After water was added, the mixture was washed with water, after which the solvent was removed and the residue was subjected to silica gel column chromatography to yield 0.11 g of a crystal. |
Here is a chemical reaction formula: Reactants are:m1_m3:NC1=C(C(=O)C2=C(C=CC=C2)OC)C=C(C=C1)Cl;m2:C([O-])(O)=O.[Na+], Reagents are:m1_m3:Br, and Products are 0:NC1=C(C(=O)C2=C(C=CC=C2)O)C=C(C=C1)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 2.15 g of 2-amino-5-chloro-2'-methoxybenzophenone and 20 ml of 47% hydrogen bromide was heated for 1 hour under reflux. The solution was rendered neutral with sodium bicarbonate, and subjected to extraction with 100 ml of ethyl acetate. The extract solution was washed with water and dried over anhydrous magnesium sulfate; the solvent was then distilled off under reduced pressure. The residue was purified by means of silica gel column chromatography (eluent, hexane:ethyl acetate=10:1) to yield 1.9 g of 2-amino-5-chloro-2'-hydroxybenzophenone as needles, m.p. 51° to 52° C. |
Here is a chemical reaction formula: Reactants are:m2:[OH-].[Na+];m1_m3:C(C)(=O)NC1=C(C(=O)C2=C(C=CC=C2)OC)C=C(C=C1)Cl, Reagents are:m1_m3:Br, and Products are 0:NC1=C(C(=O)C2=C(C=CC=C2)O)C=C(C=C1)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 10 g of 2-acetylamino-5-chloro-2'-methoxybenzophenone and 100 ml of 47% hydrogen bromide was heated for 2 hours under reflux. The solution was rendered neutral with sodium hydroxide, and was subjected to extraction with 200 ml of ethyl acetate. The extract solution was washed with water and dried over anhydrous magnesium sulfate; the solvent was then distilled off under reduced pressure. The residue was purified by means of silica gel column chromatography (eluent, hexane:ethyl acetate=5:1) to yield 8.0 g of 2-amino-5-chloro-2'-hydroxybenzophenone as needles. |
Here is a chemical reaction formula: Reactants are:m2:[BH4-].[Na+];m3_m1:NC1=C(C=C(C=C1)Br)C=1C(=NC=CC1)C(=O)C1=NC=CC=C1C1=C(C=CC(=C1)Br)N;m3_m1:CO, Reagents are:, and Products are 0:NC1=C(C(C2=NC=CC=C2)O)C=C(C=C1)Br, please give me the reaction condition of this formula. | The condition of this chemical reaction is: In 100 ml of methanol was dissolved 10 g of 2-amino-5-bromophenyl-2-pyridylketone. To the solution was added 1.7 g of sodium borohydride and stirred for 30 minutes. The solvent methanol was evaporated off under reduced pressure. The residue was treated with an aqueous solution of hydrochloric acid. The decomposed residue was then neutralized with 200 ml of a sodium bicarbonate aqueous solution, and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent, hexane:ethyl acetate=2:1) to give 2-amino-5-bromo-α-(2-pyridyl)benzyl alcohol (9.0 g) as prisms, m.p. 104°-105° C. |
Here is a chemical reaction formula: Reactants are:m3_m2:NC1=C(C(C2=NC=CC=C2)O)C=C(C=C1)Br;m3_m2:C(C)(=O)O, Reagents are:, and Products are 0:NC1=C(C(C2=NC=CC=C2)O)C=C(C=C1)Br;0:CC(C=O)(C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: In 20 ml of acetic acid was dissolved 2.0 g of 2-amino-5-bromo-α-(2-pyridyl)benzyl alcohol obtained in (1) together with 0.86 ml of trimethylacetoaldehyde. To the solution was added 0.36 g of sodium borohydride under ice-cooling. The reaction mixture was stirred for 30 minutes at room temperature and then subjected to extraction with a mixture of 100 ml of water and 150 ml of ethyl acetate. The ethyl acetate layer was washed with 1N sodium hydroxide, dried over anhydrous magnesium sulfate, and concentrated to dryness under reduced pressure. The residue was purified by silica gel column chromatography (eluent, hexane:ethyl acetate=5:1) to afford 5-bromo-2-neopentylamino-α-(2-pyridyl)benzyl alcohol (2.4 g) as an oily product. |
Here is a chemical reaction formula: Reactants are:m5_m1_m2:ClC=1C=CC2=C([C@H](O[C@@H](C(N2CC(C)(C)C)=O)CC(=O)O)C2=C(C=CC=C2)Cl)C1;m5_m1_m2:CN1CCOCC1;m3:C(OCC)(=O)Cl;m4_m6:[BH4-].[Na+], Reagents are:m5_m1_m2:O1CCCC1;m4_m6:CO, and Products are 0:ClC=1C=CC2=C([C@H](O[C@@H](C(N2CC(C)(C)C)=O)CCO)C2=C(C=CC=C2)Cl)C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: In 200 ml of tetrahydrofuran was dissolved 14.7 g of trans-7-chloro-5-(2-chlorophenyl)-1-neopentyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetic acid obtained in Example 2 and 4.51 ml of N-methylmorpholine. To the solution was added 3.92 ml of ethyl chlorocarbonate at -10° C.; the mixture was then stirred for 15 minutes. After the addition of 3.86 g of sodium borohydride, 200 ml of methanol was added dropwise to the solution. The mixture was stirred for one hour at room temperature and then concentrated. After the addition of 200 ml of 1N hydrochloric acid, the concentrate was extracted with 200 ml of ethyl acetate. The organic layer was washed with a saturated sodium bicarbonate aqueous solution and dried over anhydrous magnesium sulfate. The solvent was evaporated off under reduced pressure. The residue was purified by silica gel column chromatography (eluent, hexane:ethyl acetate=1:1) to yield 14.2 g of trans-7-chloro-5-(2-chlorophenyl)-1-neopentyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-ethanol as colorless crystals, m.p. 157° to 159° C. |