Studies on Prodrugs. III. A Convenient and Practical Preparation of Ampicillin Prodrugs

Shoji Ikeda; Fumio Sakamoto; Hirosato Kondo; Masaru Moriyama; Goro Tsukamoto

doi:10.1248/cpb.32.4316

Studies on Prodrugs. III. A Convenient and Practical Preparation of Ampicillin Prodrugs

Shoji Ikeda, Fumio Sakamoto, Hirosato Kondo, Masaru Moriyama, Goro Tsukamoto

Research output: Contribution to journal › Article

16 Citations (Scopus)

Abstract

In order to prepare ampicillin prodrugs conveniently for practical use, a new synthetic method for 6β-aminopenicillanic acid (6-APA) esters as key intermediates of various ampicillin prodrugs has been 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, bacampicillin, talampicillin and pivampicillin have been obtained in good yields by this procedure.

Original language	English
Pages (from-to)	4316-4322
Number of pages	7
Journal	Chemical and Pharmaceutical Bulletin
Volume	32
Issue number	11
DOIs	https://doi.org/10.1248/cpb.32.4316
Publication status	Published - Jan 1 1984
Externally published	Yes

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All Science Journal Classification (ASJC) codes

Chemistry(all)
Drug Discovery

Cite this

Ikeda, S., Sakamoto, F., Kondo, H., Moriyama, M., & Tsukamoto, G. (1984). Studies on Prodrugs. III. A Convenient and Practical Preparation of Ampicillin Prodrugs. Chemical and Pharmaceutical Bulletin, 32(11), 4316-4322. https://doi.org/10.1248/cpb.32.4316

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10.1248/cpb.32.4316