Dimethylformamide → HCID 70074385, compound

Participants

Reaction Steps

1.40 g (8.04 mmol) of 1,1'-carbonyldiimidazole were added to a solution of 1.42 g (8.07 mmol) of BOC-glycine in 13 ml of dimethylformamide and the mixture was stirred at 50° for 30 minutes. Subsequently, 2.30 g (7.58 mmol) of (E)- and/or (Z)- (S)-1-(aminohydroxyimino-methyl)-10,11,12,12a-tetrahydro-8H-imidazo[5,1-c]pyrrolo-[1,2-a]thieno[3,2-e][1,4]diazepin-8-one were added thereto and the mixture was stirred at 90° for 15 hours. The brown solution obtained was evaporated in a high vacuum and the brown residue obtained was chromatographed (silica gel, methylene chloride/methanol 10:1). There were obtained 1.50 g (44%) of (S)-1-(5-BOC-aminomethyl-1,2,4-oxadiazol-3-yl)-10,11,12,12a-tetrahydro-8H-imidazo[5,1-c]pyrrolo[1,2-a]thieno[3,2-e][1,4]diazepin-8-one as a colourless foam, Rf=0.62 (silica gel, methylene chloride/methanol 10:1).

Provenance & Evidence