Process for preparing 7-substituted-amino-3-hydroxy-3-cephem-4-p

Details Process for preparing 7-substituted-amino-3-hydroxy-3-cephem-4-p Process for preparing 7-substituted-amino-3-hydroxy-3-cephem-4-p

1992-11-13

1994-09-27

Rizzo, Nicholas S.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

540222, 540221, C07D50104

Patent

active

053508459

ABSTRACT:
A process for the conversion of a 4-chlorosulfonyl azetidinone (a) to a 3-hydroxy-3-cephem-sulfoxide ester (d) by subjecting an intermediate comprising a tin containing Lewis acid-type Fiedel-Crafts catalyst and 3-exomethylene cepham to ozonolysis.

REFERENCES:
patent: 3917587 (1975-11-01), Chauvette
patent: 4031084 (1977-06-01), Kukolja et al.
patent: 4052387 (1977-10-01), Kukolja
patent: 4075203 (1978-02-01), Chou
patent: 4081440 (1978-03-01), Kukolja
patent: 4115643 (1978-09-01), Kukolja et al.
patent: 4190724 (1980-02-01), Chou
patent: 4289695 (1981-09-01), Chou
patent: 4950753 (1990-08-01), Copp et al.
Journal of Medicinal Chemistry, Chemistry of Cephalosporin Antibiotics. 30 3-Methoxy-and 3-Halo-3-cephems; Chauvette and Pennington vol. 18 No. 4 pp. 403-408 (1975).
J. Org. Chem., Kukolja et al.; Synthesis of 3-Hydroxy-, 3-Chloro-, and 3-Methoxy-3-cephems from Penicillins via 4-Dithio-2-azetidinone Intermediates vol. 41 pp. 2276-2278 (1976).
Chem. Pharm. Bull., No. 2; Synthesis of 7.beta.-[(Z)-2-(2-Amino-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-c arboxylic Acid (Ceftizoxime), a New Semisynthetic Cephalosporin Antibiotic. Kobayashi et al. vol. 36 pp. 582-590 (1988).

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