Organic compounds -- part of the class 532-570 series – Organic compounds – Chalcogen in the nitrogen containing substituent
Patent
1993-07-16
1995-01-31
Shah, Mukund J.
Organic compounds -- part of the class 532-570 series
Organic compounds
Chalcogen in the nitrogen containing substituent
540200, 540357, C07D26506, C07D26508
Patent
active
053860292
ABSTRACT:
The invention relates to a novel process for the manufacture of (3R,1'R)-4-acyloxy-3-(1'-hydroxyethyl)-2-azetidinones of formula ##STR1## in which R.sup.1 represents lower alkyl or aryl, by enantioselective reduction of the carbonyl group in a suitable .alpha.-acylaminomethyl-acetoacetic acid ester, cyclization of the resulting .alpha.-acylaminomethyl-.beta.-hydroxybutyric acid ester to a 5,6-dihydro-1,3,4H-oxazine with inversion of the carbon atom carrying the hydroxy group, equilibration to form the preferred trans-substituted dihydrooxazine, recleaving to form the configuratively uniform .alpha.-aminomethyl-.beta.-hydroxybutyric acid, ring-closure to form the .beta.-lactam and oxidative acylation at C(4) of the .beta.-lactam. Compounds of formula I can be used as starting materials for the manufacture of .beta.-lactam antibiotics. The invention relates also to novel intermediates.
Ramos Gerardo
Schneider Peter
Ciba-Geigy Corporation
Fishman Irving M.
Grumbling Matthew V.
Kaiser Karen G.
Shah Mukund J.
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