Chloroacetonitrile → HCID 9979758, compound

Participants

Reaction Steps

1,3-Dihydro-3(R,S)-[(benzyloxycarbonyl)amino]-5-phenyl-2H-1,4-benzodiazepin-2-one (1.5 g) was dissolved in 25 ml of dry N,N-dimethylformamide at 0° C. To this solution was added 218 mg of (60%) sodium hydride and the resulting reaction mixture was stirred for 15 minutes. Chloroacetonitrile in 1 ml of dry N,N-dimethylformamide was then added and the reaction mixture was allowed to warm to room temperature. After 1 hour the reaction mixture was concentrated under reduced pressure and the residue was partitioned between ethyl acetate and 10% citric acid solution. The organic phase was washed with brine, then dried (sodium sulfate), and concentrated to give a solid. The title compound (1.53 g, 93%) was obtained in pure form after flash silica gel chromatography employing ethyl acetate-hexane (1:2 v/v) as eluant.

Provenance & Evidence