Process for the ring expansion of penicillins to cephalosporin c

Details Process for the ring expansion of penicillins to cephalosporin c Process for the ring expansion of penicillins to cephalosporin c

1974-01-04

1976-11-23

Rizzo, Nicholas S.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260239A, 2602391, C07D50110

Patent

active

039936465

ABSTRACT:
A process for producing a 2-cephem or 3-cephem derivative compound of the formula: ##SPC1##
Wherein R.sub.1 represents a substituted or unsubstituted amino radical and R.sub.4 represents hydrogen or a radical selected from the group consisting of carboxy, protected carboxy, ester, acid amide, acid anhydride, acid halide, acid azide and carboxy salt, and the dotted line indicates the alternate bond structure providing 3-cephem or 2-cephem, which comprises:
Reacting a halogenated derivative selected from the group consisting of a halogenated penam derivative having the formula: ##SPC2##
A halogenated cepham derivative of the formula: ##SPC3##
Wherein X represents a halogen atom, R.sub.3 represents a radical selected from the group consisting of carboxy, protected carboxy, ester, acid amide, acid anhydride, acid halide, acid azide and carboxy salt, and R.sub.1 is as defined above, or mixtures thereof with a dehydrohalogenoic acid reagent.

REFERENCES:
patent: 3725397 (1973-04-01), Graham et al.
patent: 3725399 (1973-04-01), Ellerton et al.
patent: 3843637 (1974-10-01), Rubinfeld et al.
patent: 3843639 (1974-11-01), Sapino, Jr. et al.
patent: 3862181 (1975-01-01), Davis et al.
patent: 3936447 (1976-02-01), Petersen et al.
Morrison et al., "Organic Chemistry" 1966, p. 155.

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