Dimethylformamide → HCID 70076866, compound

Participants

Reaction Steps

2.7 g (16.9 mmol) of 1,1'-carbonyldiimidazole were added to a solution of 4.5 g (14.1 mmol) of BOC-glycine in 30 ml of dimethylformamide and the mixture was stirred at 50° for 30 minutes. Subsequently, 4.5 g (14.1 mmol) of (E)- and/or (Z)-(S)-1-(aminohydroxylimino-methyl)-7,8-difluoro-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one were added and the mixture was stirred at 90° for 16 hours. The brown solution obtained was evaporated in a high vacuum and the brown residue obtained was chromatographed (silica gel, methylene chloride/methanol 19:1). There were obtained 4.9 g (76%) of (S)-1-(5-BOC-aminomethyl-1,2,4-oxadiazol-3-yl)-7,8-difluoro-12,12a-dihydro-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one as a colourless foam, Rf=0.21 (silica gel, methylene chloride/methanol 19:1).

Provenance & Evidence