Phenylacetic Acid → HCID 13631278, compound

Participants

Reaction Conditions

Reaction Steps

(S)-3-Amino-N-(aminosulfonyl)-2-oxo-1-azetidinecarboxamide (see example 22, or prepared by hydrogenating 140 mg of (S)-N-(aminosulfonyl)-3-[[(phenylmethoxy)carbonyl]amino]-2-oxo-1-azetidinecarboxamide in dimethylformamide used 50 mg of 5% palladium on charcoal catalyst) was acylated with 100 mg of dicyclohexylcarbodiimide, 20 mg of hydroxybenzotriazole and 55 mg of benzeneacetic acid. The mixture was stirred at 0° C. for 6 hours and dicyclohexylurea was filtered off. Dimethylformamide was distilled off, the residue was dissolved in 5 ml of acetone and the solution was, after standing for about 16 hours, filtered and then evaporated. The crude material was chromatographed on an HP-20 column eluting with water/acetone (6:4) to give 45 mg of the title compound, melting point 137° C.

Provenance & Evidence