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 › peer-review

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 - 1984
Externally published	Yes

All Science Journal Classification (ASJC) codes

Chemistry(all)
Drug Discovery

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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.",

author = "Shoji Ikeda and Fumio Sakamoto and Hirosato Kondo and Masaru Moriyama and Goro Tsukamoto",

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AU - Ikeda, Shoji

AU - Sakamoto, Fumio

AU - Kondo, Hirosato

AU - Moriyama, Masaru

AU - Tsukamoto, Goro

PY - 1984

Y1 - 1984

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AB - 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.

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

Abstract

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