Tert-butyl 2-(2-(benzyloxy)-5-(3-(4-methylpiperazin-1-yl)propoxy)benzamido)-4-phenylbenzoate → Tert-butyl 2-(2-hydroxy-5-(3-(4-methylpiperazin-1-yl)propoxy)benzamido)-4-phenylbenzoate

Participants

Reaction Steps

To a solution mixture of the obtained tert-butyl 2-(2-(benzyloxy)-5-(3-(4-methylpiperazin-1-yl)propoxy)benzamido)-4-phenylbenzoate (0.059 g) in methanol (1.0 mL) and chloroform (1.0 mL), 10% palladium-carbon (0.023 g) was added, followed by stirring under a hydrogen atmosphere at room temperature for 1 hour and 20 minutes. To the reaction mixture, 10% palladium-carbon (0.058 g) was added, followed by stirring under a hydrogen atmosphere at room temperature for 3 hours. Methanol (2.0 mL), chloroform (2.0 mL), and 10% palladium-carbon (0.055 g) were added to the reaction mixture, followed by stirring under a hydrogen atmosphere at room temperature for 2 hours and 50 minutes. To the reaction mixture, 10% palladium-carbon (0.025 g) was added, followed by stirring under a hydrogen atmosphere at room temperature for 4 hours and 30 minutes. The insoluble substance was removed by filtration, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 100-90% chloroform/methanol] to obtain 0.026 g of tert-butyl 2-(2-hydroxy-5-(3-(4-methylpiperazin-1-yl)propoxy)benzamido)-4-phenylbenzoate.

Provenance & Evidence