Pyridine → HCID 70509313, compound

Participants

Reaction Steps

Freshly prepared benzhydryl 1-hydroxy-2-methylcarbapenam-3-carboxylate (53 mg., 0.15 mmoles) was dissolved in 5 ml. of methylene chloride and cooled to -10° C. Pyridine (12 mg., 0.15 mmoles), acetic anhydride (15.4 mg., 0.15 mmoles) and 4-dimethylaminopyridine (18.4 mg., 0.15 mmoles) were added and the mixture stirred for 1 hour at -10° C., at which time tlc (4:1 chloroform:ethyl acetate) indicated clean conversion to the acetate ester. The reaction mixture was chromatographed on silicia gel (9:1 methylene chloride:ethyl acetate eluant), yielding purified benzhydryl 1-acetoxy-2-methylcarbapenam-3-carboxylate [Rf 0.65 (4:1 chloroform:ethyl acetate)].

Provenance & Evidence