Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1987-06-16
1989-08-08
Rizzo, Nicholas S.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
540310, 540312, 540219, C07D49942, C07D50114
Patent
active
048554197
ABSTRACT:
The present invention relates to a method for producing novel 4-[1-oxoalkyl]-2,5-oxazolidinediones, (4-1 OOD), and their use in a stereoselective method of producing beta-lactam-containing compounds which include several biologically active compounds such as the well-known families of penicillin and cephalosporin antibiotics. The method of the present invention involves generally the reaction of the above-described 4-[1-oxoalkyl]-2,5-oxazolidinediones so produced with a thiol amine having a geometry amenable to forming the precursor of the desired beta-lactam-containing compound or, in one scheme, forming the beta-lactam-containing compound itself directly. This is done either by direct reaction of the 4-1 OOD with a thiol amine (which by one pathway proceeds directly to the beta-lactam-containing compound) or by first converting the 4-1 OOD to its 2-[1-oxoalkyl]-2-amino acid form before its reaction with the thiol amine; and then forming the beta lactam by action of cyanogen). The beta-lactam-containing compounds can be further modified according to methods known in the art to produce specific derivatives as desired.
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Day Richard A.
Wallace John
Rizzo Nicholas S.
University of Cincinnati
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