反应详情

8.41 g (48 mmol) of BOC-glycine were dissolved in 30 ml of N,N-dimethylformamide and treated portionwise with 7.8 g (48 mmol) of 1,1'-carbonyldiimidazole. After completion of the CO2 evolution the solution was stirred at 45° for 10'. Then, 12.05 g (40 mmol) of (S)-7-fluoro-12,12a-dihydro-9-oxo-9H,11H-azeto-[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxamidoxime were added and the mixture was stirred at 90° overnight. By evaporation of the solution, chromatography of the residue on 550 g of silica gel while eluting with methylene chloride/methanol 19/1 and recrystallization from ethyl acetate there were obtained 10.78 g (61%) of (S)-1-[5-(BOC-aminomethyl)-1,2,4-oxadiazol-3-yl]-7-fluoro-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one of m.p. 147°-150°.

1. customBy evaporation of the solution, chromatography of the residue on 550 g of silica gel
2. washwhile eluting with methylene chloride/methanol 19/1 and recrystallization from ethyl acetate