Dimethylformamide → (S)-8-chloro-7-fluoro-12,12a-dihydro-1-(3-phthalimidomethyl-1,2,4-oxadiazol-5-yl)-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one

Participants

Reaction Steps

10 g (31.09 mmol) 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-carboxylic acid were dissolved in 100 ml of N,N-dimethylformamide, treated portionwise with 6.05 g (37.3 mmol) of 1,1'-carbonyldiimidazole and stirred at room temperature for 1 hour. After adding 6.8 g (31.09 mmol) of phthaloylglycine amidoxime the mixture was stirred at room temperature overnight, 10 ml of trifluoroacetic acid were added and the mixture was stirred at 90° overnight. After evaporating the solvent the residue was crystallized from methylene chloride and methanol. There were obtained 8.55 g (54%) of (S)-8-chloro-7-fluoro-12,12a-dihydro-1-(3-phthalimidomethyl-1,2,4-oxadiazol-5-yl)-9H,11H-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one of m.p. 292°-294°.

Provenance & Evidence