Process for the manufacture of 4-acetoxy-3-hydroxyethyl-azetidin

Details Process for the manufacture of 4-acetoxy-3-hydroxyethyl-azetidin Process for the manufacture of 4-acetoxy-3-hydroxyethyl-azetidin

1992-08-27

1994-05-17

Berch, Mark L.

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

Organic compounds

Unsubstituted hydrocarbyl chain between the ring and the -c-...

204 59R, 549321, 560170, 562568, C07D20508, C07D30766, C07B 5300

Patent

active

053129148

ABSTRACT:
The invention relates to a novel process for the manufacture of 4-acetoxy-3-hydroxyethyl-azetidinone of the formula ##STR1## especially 4(R)-acetoxy-3(R)-(1'(R)-hydroxyethyl)-2-azetidinone, from enantiomerically pure compounds of the formula ##STR2## in which R.sup.1 represents lower alkyl and Z.sup.1 represents amino, arylmethylamino, acylamino or azido, by reduction of the C.dbd.C double bond and optionally of the arylmethylamino or azido group with hydrogen, epimerization, opening of the lactone ring, cyclisation to the .beta.-lactam, optionally after hydrolysis of the acylamino group, and oxidative decarboxylation of the original lactone carboxy group in the presence of an acetate-yielding agent. Compounds of the formula I can be used as starting materials for the manufacture of .beta.-lactam antibiotics. The invention also relates to novel intermediates and starting materials.

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