Cephem compound, its production and its use for producing...

C - Chemistry – Metallurgy – 07 – D

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C07D 501/16 (2006.01) C07D 501/00 (2006.01) C07D 519/00 (2006.01) C07F 7/10 (2006.01)

Patent

CA 2127902

ABSTRACT A 3-[(E)-1-propenyl]cephem compound represented by formula (I): Image (I) wherein R represents hydrogen, a protective group for an amino group, or the group shown by formula (II): Image (II) in which R3 is a protective group for an amino group, R4 is a protective group for a hydroxyl group, and W is -CH= or -N=; R2 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.

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