Studies on the Stability of Δ2 and Δ3 Cephem Esters. I. Marked Difference in Stability between Δ2 and Δ3 Cephem Prodrug Esters and Application to the Preparation of Key Intermediates for Oral Cephem Synthesis

Shigeto NEGI; Mototuske YAMANAKA; Yuki KOMATSU; Akihiko TSURUOKA; Itaru TSUKADA; Norio MINAMI

doi:10.1248/cpb.43.1998

Studies on the Stability of Δ² and Δ³ Cephem Esters. I. Marked Difference in Stability between Δ² and Δ³ Cephem Prodrug Esters and Application to the Preparation of Key Intermediates for Oral Cephem Synthesis

Shigeto NEGI, Mototuske YAMANAKA, Yuki KOMATSU, Akihiko TSURUOKA, Itaru TSUKADA, Norio MINAMI

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Keywords: antibacterial agent, oral cephalosporin, practical synthesis

JOURNAL FREE ACCESS

1995 Volume 43 Issue 11 Pages 1998-2000

DOI https://doi.org/10.1248/cpb.43.1998

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Abstract

The esterification of Δ³-cephem-4-carboxylic acid sodium salt (1) with 1-iodoethyl isopropyl carbonate always afforded the Δ² cephem ester (3) as an inseparable minor component. However, in the course of formamido cleavage reaction, the 7-amino-Δ²-cephem ester (5) was observed to be less stable than the Δ³ cephem ester (4), which led us to develop a practical synthetic process for Δ³ cephem esters, including a key intermediate of E1101, a new oral cephalosporin.

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