Pyridine → 4-Nitrobenzyl 7-amino-3-chloro-3-cephem-4-carboxylate hydrochloride

Participants

Reaction Steps

To a solution of 500 mg. of p-nitrobenzyl 7-[2-(2-thienyl)acetamido]-3-chloro-3-cephem-4-carboxylate in 6 ml. of methylene chloride was added 95 mg. of dry pyridine and 237 mg. of phosphorus pentachloride. The reaction mixture was stirred at room temperature for 1.5 hours, was thereafter cooled in an ice-water bath to about 5° C. and 0.6 ml. of iso-butyl alcohol were added. On continued cooling and stirring the reaction product, p-nitrobenzyl 7-amino-'-chloro-3-cephem-4-carboxylate hydrochloride, crystallized from the reaction mixture. The product was filtered, washed with cold methylene chloride and dried to yield 200 mg. of the crystalline product melting with decomposition at about 168° C.

Provenance & Evidence