ethyl 3-bromo-2-oxo-4-phenylbutanoate

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of ethyl 3-bromo-2-oxo-4-phenylbutanoate (13.8 g, 48.4 mmol) in MeOH (161 mL) was slowly added 2,5-difluorobenzothioamide (8.38 g, 48.4 mmol) at room temperature. The reaction mixture was then refluxed for overnight. After cooled down, white precipitate was filtered, washed by cold ethanol and dried. A mixture of methyl 5-benzyl-2-(2,5-difluorophenyl)thiazole-4-carboxylate and ethyl 5-benzyl-2-(2,5-difluorophenyl)thiazole-4-carboxylate (10.5 g, 61%) was obtained as white solid. LC/MS (uplc): MW 346.1, 1.21 min for methyl ester; 360.1, 1.27 min for ethyl ester. at room temperature The reaction mixture was then refluxed for overnight After cooled down white precipitate was filtered washed by cold ethanol dried A mixture of methyl 5-benzyl-2-(2,5-difluorophenyl)thiazole-4-carboxylate

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of ethyl 3-bromo-2-oxo-4-phenylbutanoate (13.8 g, 48.4 mmol) in MeOH (161 mL) was slowly added 2,5-difluorobenzothioamide (8.38 g, 48.4 mmol) at room temperature. The reaction mixture was then refluxed for overnight. After cooled down, white precipitate was filtered, washed by cold ethanol and dried. A mixture of methyl 5-benzyl-2-(2,5-difluorophenyl)thiazole-4-carboxylate and ethyl 5-benzyl-2-(2,5-difluorophenyl)thiazole-4-carboxylate (10.5 g, 61%) was obtained as white solid. LC/MS (uplc): MW 346.1, 1.21 min for methyl ester; 360.1, 1.27 min for ethyl ester. at room temperature The reaction mixture was then refluxed for overnight After cooled down white precipitate was filtered washed by cold ethanol dried A mixture of methyl 5-benzyl-2-(2,5-difluorophenyl)thiazole-4-carboxylate

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Ethyl 3-bromo-2-oxo-4-phenylbutanoate (5.8 g) was dissolved in EtOH (110 ml), and then thiourea (3.1 g) was added to the solution. The reaction mixture was refluxed for 2 hours under N2 atmosphere. The cooled reaction mixture was evaporated in vacuo. The residual solid was suspended (pH=8) in saturated NaHCO3 and water. The solid was collected by filtration, and purified by flash column chromatography over silica gel with CHCl3/MeOH (10:1) as an eluent to give ethyl 2-amino-5-benzyl-1,3-thiazole-4-carboxylate (808.2 mg) as a yellow wax. The reaction mixture was refluxed for 2 hours under N2 atmosphere The cooled reaction mixture was evaporated in vacuo The solid was collected by filtration purified by flash column chromatography over silica gel with CHCl3/MeOH (10:1) as an eluent

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Ethyl 3-bromo-2-oxo-4-phenylbutanoate (5.8 g) was dissolved in EtOH (110 ml), and then thiourea (3.1 g) was added to the solution. The reaction mixture was refluxed for 2 hours under N2 atmosphere. The cooled reaction mixture was evaporated in vacuo. The residual solid was suspended (pH=8) in saturated NaHCO3 and water. The solid was collected by filtration, and purified by flash column chromatography over silica gel with CHCl3/MeOH (10:1) as an eluent to give ethyl 2-amino-5-benzyl-1,3-thiazole-4-carboxylate (808.2 mg) as a yellow wax. The reaction mixture was refluxed for 2 hours under N2 atmosphere The cooled reaction mixture was evaporated in vacuo The solid was collected by filtration purified by flash column chromatography over silica gel with CHCl3/MeOH (10:1) as an eluent

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of ethyl 3-bromo-2-oxo-4-phenylbutanoate (13.8 g, 48.4 mmol) in MeOH (161 mL) was slowly added 2,5-difluorobenzothioamide (8.38 g, 48.4 mmol) at room temperature. The reaction mixture was then refluxed for overnight. After cooled down, white precipitate was filtered, washed by cold ethanol and dried. A mixture of methyl 5-benzyl-2-(2,5-difluorophenyl)thiazole-4-carboxylate and ethyl 5-benzyl-2-(2,5-difluorophenyl)thiazole-4-carboxylate (10.5 g, 61%) was obtained as white solid. LC/MS (uplc): MW 346.1, 1.21 min for methyl ester; 360.1, 1.27 min for ethyl ester. at room temperature The reaction mixture was then refluxed for overnight After cooled down white precipitate was filtered washed by cold ethanol dried A mixture of methyl 5-benzyl-2-(2,5-difluorophenyl)thiazole-4-carboxylate