Process for producing 1-beta-methylcarbapenem antibiotic interme

Details Process for producing 1-beta-methylcarbapenem antibiotic interme Process for producing 1-beta-methylcarbapenem antibiotic interme

1987-12-16

1989-03-28

Berch, Mark L.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07B 5500, C07D20508, C07F 720, C07F 718

Patent

active

048165778

ABSTRACT:
A process for isomerizing an alpha methylated azetidinone alkyl ester to the corresponding beta-methyl isomer, which is an intermediate in the synthesis of 1-beta-methylcarbapenem antibacterial agents. The process involves treating the dianion of structure I, being the alpha isomer, with a P-H or S-H containing organic protic acid, organometallic Sn or Pb hydride, metallic cation salt or trialkyl borane, followed by quenching with an OH protic organic acid or mineral acid.

REFERENCES:
Heterocycles, vol. 21, No. 1, 1984 by David Shih, et al.
Tetrahedron Letters, vol. 26, No. 14, pp. 1739-1742, 1985 by Hideo Hirai, et al.

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