1-Hydroxybenzotriazole → 1-tert-butylcarbonylmethyl-2-oxo-3-[(2S)-(2-tert-butoxycarbonylamino-3-phenylpropionyl)amino]-5-phenyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

Participants

Reaction Steps

1-tert-Butylcarbonylmethyl-2-oxo-3-amino-5-phenyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (3.62 g) was dissolved in anhydrous N,N-dimethyl formamide (30 ml) under argon atmosphere, N-tert-butoxycarbonyl-L-phenylalanine (3.00 g), 1-hydroxybenzotriazole (1.73 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.17 g) and triethylamine (2.08 g) were added at ice-cooling, thereto the mixture was stirred for 5 minutes under ice-cooling, and stirred at room temperature for one hour. Water and ethyl acetate were added to the reaction mixture, separated, the organic layer was successively washed with water and saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1), to thereby obtain 6.17 g of the title compound.

Provenance & Evidence