4-Methylmorpholine → HCID 131717475, compound

Participants

Reaction Steps

To a suspension of 7β-amino-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester (1) hydrochloride (72.1 g; 171 mMol.) in dichloromethane (1200 ml) are added N-methylmorpholin (18.8 ml; 1 Eq.) and 2-(2-t-butoxycarbonylamino-4-thiazolyl)-2-(1-diphenylmethoxycarbonyl-1-methylethoxyimino)acetic acid (95.5 g; 1.3 Eq.) at 0° C. and then phenylphosphoric acid dichloride (33.2 ml; 1.3 Eq.) and N-methylmorpholin (56.4 ml; 3 Eq.) at -40° C., and the mixture is stirred at -40° to -25° C. for 50 minutes. The reaction mixture is diluted with water. The formed dichloromethane layer is taken, washed with hydrochloric acid, water, aqueous sodium hydrogen carbonate, and water, dried, and concentrated under reduced pressure to give 7β-[2-(2-t-butoxycarbonylaminothiazol-4-yl)-2-(1-diphenylmethoxycarbonyl-1-methylethoxyimino)acetamido]-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester (2) (165 g).

Provenance & Evidence