Pyridine → HCID 86738682, compound

Participants

Reaction Steps

Dicyclohexylcarbodiimide (1.8 g.) and pyridine (0.23 g.) were added to a solution of diphenylmethyl 7-(2-phenylacetamido)-3-hydroxymethylcepham-4-carboxylate (1.5 g.) in dimethylsulfoxide (7 ml.) and benzene (15 ml.). To the solution was added trifluoroacetic acid (0.17 g.) and the mixture was stirred at room temperature overnight. After filtration, the filtrate was poured in a mixture of ethyl acetate (100 ml.) and water (100 ml.). The solution was adjusted to pH 3.0, and the ethyl acetate layer was separated, washed with aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated in vacuo. The insoluble substance was removed by filtration and the filtrate was subjected to column chromatography on silica gel and eluted with a mixture of ethyl acetate and methylene chloride. The eluate was concentrated in vacuo to give diphenylmethyl 7-(2-phenylacetamido)-3-formylcepham-4-carboxylate (0.6 g.).

Provenance & Evidence