Cephem compound, its production and its use for producing cephem

Details Cephem compound, its production and its use for producing cephem Cephem compound, its production and its use for producing cephem

1997-09-18

1999-10-19

Berch, Mark L.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

540222, C07D50120, C07D50104

Patent

active

059691310

ABSTRACT:
A 3-[(E)-1-propenyl]cephem compound represented by formula (I): ##STR1## wherein R represents hydrogen, a protective group for an amino group, or the group shown by formula (II): ##STR2## in which R.sup.3 is a protective group for an amino group, R.sup.4 is a protective group for a hydroxyl group, and W is --CH.dbd. or --N.dbd.; R.sup.2 represents a protective group for a carboxyl group; and X represents hydrogen or chlorine. The compound is useful as an intermediate for producing cephem antibiotics and is prepared by isomerizing the corresponding 3-[(Z)-1-propenyl]cephem compound in an inert organic solvent in the presence of an aromatic thiol. The compound of formula (I) wherein X is chlorine can be converted into a 3-[(E)-3-ammonio-1-propenyl]cephem derivative through the reaction with a tertiary amine.

REFERENCES:
patent: 4486586 (1984-12-01), Narita
patent: 4751295 (1988-06-01), Oka
patent: 4874856 (1989-10-01), Iimura
patent: 5095012 (1992-03-01), Okita
patent: 5373000 (1994-12-01), Machida
patent: 5373001 (1994-12-01), Aszodi
patent: 5401841 (1995-03-01), Asher
Schwartz, J. Org. Chem 51, 260, 1986.
Seymour Mark, Stereoisomerism In Pharmaceuticals, The Pharmaceutical Journal, Jan. 6, 1990, pp. 25-29.
M. Schwarz et at., "Insect Sex Pheromones. Stereospecific Synthesis of (E)-13, 13-Dimethyl-11-tetradecen-1-01 Acetate via a Thiophenol-Mediated Olefin Inversion", J. Org. Chem., vol. 51, No. 2, 1986, pp. 260-263.

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