STUDIES ON THE STABILITY OF DELTA(2) AND DELTA(3) CEPHEM ESTERS .1. MARKED DIFFERENCE IN STABILITY BETWEEN DELTA(2) AND DELTA(3) CEPHEM PRODRUG ESTERS AND APPLICATION TO THE PREPARATION OF KEY INTERMEDIATES FOR ORAL CEPHEM SYNTHESIS

Authors
NEGI S YAMANAKA M KOMATSU Y TSURUOKA A TSUKADA I MINAMI N
Citation
S. Negi et al., STUDIES ON THE STABILITY OF DELTA(2) AND DELTA(3) CEPHEM ESTERS .1. MARKED DIFFERENCE IN STABILITY BETWEEN DELTA(2) AND DELTA(3) CEPHEM PRODRUG ESTERS AND APPLICATION TO THE PREPARATION OF KEY INTERMEDIATES FOR ORAL CEPHEM SYNTHESIS, Chemical and Pharmaceutical Bulletin, 43(11), 1995, pp. 1998-2000
Citations number
8
Categorie Soggetti
Pharmacology & Pharmacy",Chemistry
Journal title
Chemical and Pharmaceutical Bulletin → ACNP
ISSN journal
00092363
Volume
43
Issue
11
Year of publication
1995
Pages
1998 - 2000
Database
ISI
SICI code
0009-2363(1995)43:11<1998:SOTSOD>2.0.ZU;2-J
Abstract
The esterification of Delta(3)-cephem-4-carboxylic acid sodium salt (1 ) with 1-iodoethyl isopropyl carbonate always afforded the Delta(2) ce phem ester (3) as an inseparable minor component, However, in the cour se of formamido cleavage reaction, the 7-amino-Delta(2)-cephem ester ( 5) was observed to be less stable than the Delta(3) cephem ester (4), which led us to develop a practical synthetic process for Delta(3) cep hem esters, including a key intermediate of E1101, a new oral cephalos porin.