Pyridine → HCID 70457302, compound

Participants

Reaction Conditions

Reaction Steps

A solution of the triphenyl phosphite-chlorine kinetic compound was prepared in accordance with the procedure described in Paragraph 6A above using chlorine and 2.89 ml (11 mmol) of triphenyl phosphite in 45 ml of methylene chloride. To this solution was added 2.3 gm (5 mmol) of 4'-nitrobenzyl 7-phenylacetamido-3-hydroxy-3-cephem-4-carboxylate. Then a solution of 0.89 ml (11 mmol) of pyridine and 5 ml of methylene chloride was added dropwise with stirring at -15° to -10° C. over a 15 minutes interval. After the reaction mixture was stirred for 1.5 hours at -15° to -10° C., the cooling bath was removed, and 6 ml (64.8 mmol) of isobutanol was added. As the mixture was stirred for the next hour, the mixture warming to 23° C., the product crystallized from the reaction mixture. Filtration of the mixture provided 1.59 grams (78.3%) of the nucleus ester hydrochloride as white crystals: m.p. 188° C. (dec.).

Provenance & Evidence