Pyridine → HCID 131710674, compound

Participants

Reaction Steps

To a slurry of 0.457 g. of benzhydryl 7-(2-thienylacetamido)-3-acetyl-3-cephem-4-carboxylate in 5 ml. of methylene chloride was added .085 ml. of pyridine and 0.205 g. of phosphorous pentachloride. The reaction mixture was allowed to stir for two hours at room temperature. After cooling the reaction mixture briefly in an ice bath 0.425 ml. of isobutanol was added. After allowing the reaction mixture to stir at room temperature for one hour n-hexane was added dropwise causing a precipitate which, after cooling the reaction mixture briefly in an ice bath, was isolated by decanting the supernatant liquid. The product thereby isolated was dissolved in a slurry of ethyl acetate and aqueous sodium bicarbonate. The organic layer was separated, washed with aqueous sodium bicarbonate solution and brine and then dried over anhydrous sodium sulfate. Evaporation in vacuo to dryness provided 0.270 g. (77.9 percent) of title product as a brown froth:

Provenance & Evidence