4-Methylmorpholine → HCID 131717474, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 7β-amino-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester (1) toluene-p-sulfonic acid salt (3.94 g; (7.28 mMol.) in dichloromethane (50 ml) keeping at 0° C. are added N-methylmorpholin (0.80 ml; 1 Eq.) and 2-(2-t-butoxycarbonylamino-4-thiazolyl)-2-t-butoxycarbonylmethoxyiminoacetic acid (3.80 g; 1.3 Eq.) and cooled at -40° C. To this mixture are added phenylphosphoric acid dichloride (1.41 ml; 1.3 Eq.) and N-methylmorpholin (2.41 ml; 3 Eq.), and the mixture is stirred at -40° to -15° C. for 1.5 hours. The reaction mixture is diluted with ethyl acetate, washed with water, diluted hydrochloric acid and water, dried, and concentrated under reduced pressure. The residue is purified by silica gel chromatography (toluene toluene: ethyl acetate) to give 7β-[2-(2-t-butoxycarbonylamino-4-thiazolyl)-2-t-butoxycarbonylmethoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester (2) (5.20 g).

Provenance & Evidence