Carbon Dioxide → HCID 67713734, compound

Participants

Reaction Steps

17.08 g (97 mmol) of BOC-glycine were dissolved in 165 ml of N,N-dimethylformamide and treated portionwise with 16.9 g (104 mmol) of 1,1'-carbonyldiimidazole. After completion of the CO2 evolution the solution was stirred at 50° for 30 min. Then, 30.8 g (91mmol) of (S)-8-chloro-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 and chromatography of the residue on 1.5 kg of silica gel while eluting with methylene chloride/methanol 19/1 there were obtained 36.8 g (84%) of (S)-1-[5-(BOC-aminomethyl)-1,2,4-oxadiazol-3-yl]-8-chloro-7-fluoro-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one, which was used in the next step without further purification.

Provenance & Evidence