A Practical Synthetic Method for 3-(N, N-Disubstituted Carbamoyloxy)-methyl Cephems without Generating the Δ2-Isomers

A Practical Synthetic Method for 3-(N, N-Disubstituted Carbamoyloxy)-methyl Cephems without Generating the Δ2-Isomers

E1101, a new oral caphalosporin, has a (N, N-dimethylcarbamoyloxy)methyl group at the C-3 position of the cephem nucleus. The previous methods for manufacturing 3-(N, N-disubstituted carbamoyloxy)methyl cephems generate various amounts of intractable Δ2 isomers as by-products. In this report, we des...

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Veröffentlicht in:Chemical & pharmaceutical bulletin 1995/06/15, Vol.43(6), pp.1031-1034
Hauptverfasser: NEGI, Shigeto, YAMANAKA, Motosuke, KOMATSU, Yuki, TSURUOKA, Akihiko, KAMADA, Atsushi, TSUKADA, Itaru, MACHIDA, Yoshimasa
Format: Artikel
Sprache:eng
Schlagworte:
antibacterial agent
carbamoyloxylation
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
oral cephalosporin
Organic chemistry
Preparations and properties
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Zusammenfassung:E1101, a new oral caphalosporin, has a (N, N-dimethylcarbamoyloxy)methyl group at the C-3 position of the cephem nucleus. The previous methods for manufacturing 3-(N, N-disubstituted carbamoyloxy)methyl cephems generate various amounts of intractable Δ2 isomers as by-products. In this report, we describe a new, practical synthetic method for cephems of this type without generating Δ2 isomers, via 7-acylamino-3-(4-nitrophenoxy-carbonyloxy)methyl-Δ3-cephem-4-carboxylic acid (5) as a key intermediate.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.43.1031