Hydrochloric Acid → 1-Acetoxyethyl 3-azidomethyl-7-[2-(2-tritylamino-4-thiazolyl)-2-(1-methyl-1-methoxy-ethoxyimino)-acetamido]-ceph-3-eme-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of 739 mg of 3-azidomethyl-7-[2-(2-tritylamino-4-thiazolyl)-2-(1-methyl-1-methoxy-ethoxyimino)-acetamido]-ceph-3-eme-4-carboxylic acid, 76 mg of potassium carbonate and 3 ml of dimethylformamide was stirred at 20° C. for 10 minutes and after cooling the mixture to 0° to 50° C., 0.6 g of 1-bromoethyl acetate was slowly added thereto. The mixture was stirred for 20 minutes at 0° to 5° C. and for one hour at 20° C. and then a mixture of 40 ml of iced water and 1.5 ml of N hydrochloric acid were added thereto. The mixture was vacuum filtered and the product was rinsed with water and dried to obtain 761 mg of the syn isomer of 1-acetoxyethyl 3-azidomethyl-7-[2-(2-tritylamino-4-thiazolyl)-2-(1-methyl-1-methoxy-ethoxyimino)-acetamido]-ceph-3-eme-4-carboxylate.

Provenance & Evidence