Cephalosporin intermediates

Details Cephalosporin intermediates Cephalosporin intermediates

1980-11-24

1982-06-08

Coughlan, Jr., Paul M.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

544 90, 260239A, C07D50118

Patent

active

043340652

ABSTRACT:
7.alpha.-(Dimethylamidino)-3-cephem ester 1.alpha.-oxides represented by the formula ##STR1## wherein R is hydrogen or acetoxy and R.sub.1 is a carboxy protecting group, are prepared via DBU epimerization of the corresponding 7.beta.-isomer. When R is hydrogen the intermediates are useful in the preparation of the 7.beta.-acylamino-7.alpha.-methoxy-1-oxa-.beta.-lactam antibiotics, and when R is acetoxy the compounds are intermediates to 7.beta.-acylamino-7.alpha.-methoxy-3-exomethylenecepham compounds.

REFERENCES:
patent: 4198406 (1980-04-01), Hardy et al.
J. Altman et al., "7-N-Amidinocephalosporins", J. Med. Chem., 1975, vol. 18, No. 6, pp. 627-630.
F. J. Lund, "6.beta.-Amidinopenicillanic Acids-Synthesis and Antibacterial Properties", Recent Advances in the Chemistry of .beta.-Lactam Antibiotics, Ed. J. Elks, Specialist Publication Chemical Society, No. 28, 1977, pp. 25-45.
B. Baltzer et al., "Degradation of Mecillinam in Aqueous Solution", J. Pharm. Soc., 68, No. 10, Oct., 1979, pp. 1207-1215.

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