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Prodrugs 3. a convenient and practical preparation of ampicillin prodrugs



Prodrugs 3. a convenient and practical preparation of ampicillin prodrugs



Chemical and Pharmaceutical Bulletin 32(11): 4316-4322



In order to prepare ampicillin prodrugs conveniently for practical use, a new synthetic method or 6.beta.-aminopenicillanic acid (6-APA) esters as key intermediates of various ampicillin prodrugs was developed. Acylation of 6-APA esters to ampicillin esters was achieved in good yields by using phenylglycyl chloride hydrochloride in dichloromethane in the presence of sodium bicarbonate and amide, or ammonium bicarbonate alone. KBT-1585 [ampicillin], bacampicilln, talampicilln and pivampicillin were obtained in good yields by this procedure.

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