Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1995-06-05
1997-04-29
Ivy, C. Warren
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C07D49900
Patent
active
056250592
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, 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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Bersier Jacques
Sedelmeier Gottfried
Ciba-Geigy Corporation
Covington Raymond
Ferraro Gregory D.
Ivy C. Warren
Kaiser Karen G.
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