Process for the preparation of 7-aminocephalosporanic acids

Details Process for the preparation of 7-aminocephalosporanic acids Process for the preparation of 7-aminocephalosporanic acids

1974-01-14

1976-01-13

Rizzo, Nicholas S.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

424246, 2602391, C07D27908, C07D50118

Patent

active

039323927

ABSTRACT:
7-Aminocephalosporanic acid (7-ACA) and 7-amino-3-methyl-3-cephem-4-carboxylic acid (7-ADCA) are valuable intermediates in the preparation of semi-synthetic cephalosporins. These compounds are commonly prepared by cleaving the amide bond of compounds having the formula ##SPC1##
In which R.sup.6 is H or ##EQU1## R is the side chain of a known penicillin, especially phenoxymethyl or benzyl, and the amino and carboxyl functions are blocked; by
A. halogenating the blocked compounds Ia or IIa to produce an imino-halide;
B. forming an imino-ether from the imino-halide by treatment with an alcohol; and
C. mixing said imino-ether with water or an alcohol to produce 7-aminocephalosporanic acid or 7-amino-3-methyl-3-cephem-4-carboxylic acid.
The invention claimed is the use of dicyclohexylamine or diisopropylamine instead of a tertiary amine acid scavenger in step A.

REFERENCES:
patent: 3725397 (1973-04-01), Graham et al.
patent: 3725399 (1973-04-01), Ellerton et al.

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