Intermediates for synthesis of cephalosporins and process...

Details Intermediates for synthesis of cephalosporins and process... Intermediates for synthesis of cephalosporins and process...

2002-12-26

2008-11-18

Berch, Mark L (Department: 1624)

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C540S225000, C540S227000, C540S228000, C558S028000

Reexamination Certificate

active

07452990

ABSTRACT:
A novel 4-halo-2-oxyimino-3-oxo butyric acid-N,N-dimethyl formiminium chloride chlorosulfate of formula (I) useful in the preparation of cephalosporin antibioticswhereinX is chlorine or bromine; R is hydrogen, C1-4alkyl group, an easily removable hydroxyl protective group, —CH2COOR5, or —C(CH3)2COOR5, wherein R5is hydrogen or an easily hydrolysable ester group. The compound of formula (I) is prepared by reacting 4-halo-2-oxyimino-3-oxobutyric acid of formula (IV1),wherein X, R and R5are as defined above, with N,N-dimethylformiminium chloride chlorosulphate of formula (VII)in an organic solvent at a temperature ranging from −30° C. to −15° C. The cephalosporins that may be prepared from the intermediate include cefdinir, cefditoren pivoxil, cefepime, cefetamet pivoxil, cefixime, cefmenoxime, cefodizime, cefoselis, cefotaxime, cefpirome, cefpodoxime proxetil, cefquinome, ceftazidime, cefteram pivoxil, ceftiofur, ceftizoxime, ceftriaxone and cefuzonam.

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