Dimethylformamide → HCID 70076426, compound

Participants

Reaction Steps

3.82 g (23.5 mmol) of 1,1'-carbonyldiimidazole were added to a solution of 3.85 g (21.9 mmol) of BOC-glycine in 45 ml of dimethylformamide and the mixture was stirred at 50° for 30 minutes. Subsequently, 5.7 g (20.56 mmol) of (E)- and/or (Z)-3-(aminohydroxyimino-methyl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a]thieno[2,3-f][1,4]diazepin-6-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 7.2 g (84%) of not quite pure 3-(5-BOC-aminomethyl-1,2,4-oxadiazol-3-yl)-5-methyl-5,6-dihydro-4H-imidazo[1,5-a]thieno[2,3-f][1,4]diazepin-6-one as a colourless foam, Rf=0.28 (silica gel, methylene chloride/methanol 10:1).

Provenance & Evidence