Process for chiral synthesis of 1-.beta.-methylcarbapenem interm

Organic compounds -- part of the class 532-570 series – Organic compounds – Chalcogen in the nitrogen containing substituent

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260239A, 544 69, 544 71, 546 14, 546281, 556408, C07D49801, C07F 710, C07F 718

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active

045957509

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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Shih et al., Heterocycles, vol. 21 (1984), pp. 29-40.
Feiser, Reagents for Organic Synthesis, vol. 1 (1967), John Wiley and Sons, Inc., New York, pp. 723-729.

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