O-Cresol → HCID 70133461, compound

Participants

Reaction Conditions

Reaction Steps

22.8 g of phosphorus pentachloride, 150 ml of methylenechloride, and 8.88 ml of pyridine were placed in 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 2 was dropwise added thereto and stirred for 2 hours. The reaction mixture was cooled to −10° C. and 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 thereto 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 then cooled to 0° C. An obtained 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