Chloroacetonitrile → 1-Cyanomethyl-3-(2-phenylacetamido)-2-azetidinone

Participants

Reaction Steps

3-(2-Phenylacetamido)-2-azetidinone (408 mg.) and 2-chloroacetonitrile (152 mg.) was dissolved in N,N-dimethylformamide (15 ml.), and to the solution was added sodium hydride (50% oily) (105 mg.) under stirring at ambient temperature, whereafter the reaction mixture was stirred for an hour at room temperature, and ethyl acetate (100 ml.) was added to the reaction mixture. The ethyl acetate layer was washed with water and dried over anhydrous magnesium sulfate, and then the solvent was distilled off from the solution under reduced pressure. The oily residue (0.25 g.) obtained was subjected to column chromatography using silica gel. 1-Cyanomethyl-3-(2-phenylacetamido)-2-azetidinone (56.3 mg.) was obtained from fractions eluted with chloroform. Mp 108° to 109° C. (dec.).

Provenance & Evidence