O-Cresol → HCID 70133461, compound

Participants

Reaction Conditions

Reaction Steps

22.8 g of phosphorous pentachloride, 150 ml of methylenechloride, and 8.88 ml of pyridine were added to a 20° C. reactor and stirred for 30 minutes. 30 g (62.6 mmol) of the 7-phenylacetamido-3-[propen-1-yl]-3-cephem-4-carboxylic acid p-methoxybenzyl ester prepared in Example 1 was dropwise added thereto, stirred for 2 hours, and cooled to −10° C. The reaction mixture was stirred for 2 hours after addition of 30 ml of 1,2-propanediol and then for 2 hours after addition of 120 ml of cresol. 200 ml of distilled water was dropwise added to the reaction solution and stirred for 1 hour. After phase separation, an aqueous layer was sent to a crystallization bath and an organic layer was extracted with 300 ml of 2N HCl and then the extract was sent to the crystallization bath. 200 ml of a 30% sodium hydroxide solution was dropwise added to the crystallization bath for crystallization and cooled to 0° C. to precipitate a solid. The solid was filtered and dried in vacuum to give 12 g (50 mmol, yield 80%, Z/E=10.1/1) of the titled compound as a beige solid.

Provenance & Evidence