.beta.-lactams containing an .alpha.-exocyclic double bond

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

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540300, 544 69, 544 71, 544 90, C07D49804, C07F 710

Patent

active

046171525

ABSTRACT:
A process is described for selectively obtaining 1-.beta.-methylcarbapenem intermediates. The desired chirality is obtained through the hydrogenation of certain bicyclic .beta.-lactam ring structures containing an exocyclic methylene double bond alpha to the .beta.-lactam ring, in the presence of a Group VIII metal hydrogenation catalyst. The hydrogenation results in a mixture of .alpha.- and .beta.-methyl epimers having a high .beta./.alpha. epimeric ratio. New 1-.beta.-methylcarbapenem intermediates made by the process are also described.

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patent: 4383946 (1983-05-01), Christensen et al.
patent: 4521337 (1985-06-01), Southgate et al.
Heterocycles, 1984, vol. 21, pp. 29-40, by D. H. Shih, et al.
Reagents for Organic Synthesis, vol. 1, pp. 723-729, by S. L. Feiser (1967) John Wiley and Sons, Inc., New York.

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