Pyridine → HCID 13638942, compound

Participants

Reaction Steps

A 220.3 mg (2 millimole) quantity of methyl methanesulfonate and 158.2 mg (2millimole) of dry pyridine were dissolved in 80 ml of dry dioxane, and were heated under reflux for one hour to produce N-methylpyridinium methanesulfonate. To the salt was added 914 mg (2 millimole) or the p-methoxybenzyl ester of benzylpenicillin sulfoxide and the mixture was heated under reflux for 11 hours. At this time, a condensed solvent was passed through calcium oxide before the condensed solvent was returned to the reaction container or vessel. After the completion of the reaction, the insoluble materials were removed therefrom, and the solvent was evaporated under reduced pressure. The residue was dissolved in 50 ml of ethyl acetate, and after the solution was washed with water and dried, ethyl acetate was distilled. When the product thus obtained was washed with diethyl ether, 604.7 mg (66.9%) of the p-methoxybenzyl ester of 7-phenylacetamidodesacetoxy cephalosporanic acid having a melting point of 162.5° to 168°C were obtained. The acid was very pure. However, recrystallization of the acid gave a completely pure product having a melting point of 179.5° to 181°C.

Provenance & Evidence