C - Chemistry – Metallurgy – 12 – P
Patent
C - Chemistry, Metallurgy
12
P
195/131, 204/91.
C12P 13/04 (2006.01) C07D 205/08 (2006.01) C07D 265/08 (2006.01)
Patent
CA 1335971
The invention relates to a novel process for the manufacture of (3R,1'R)- 4-acyloxy-3-(1'-hydroxyethyl)-2-azetidinones of formula Image (I) in which R1 represents lower alkyl or aryl, by enantioselective reduction of the carbonyl group in a suitable .alpha.-acylaminomethyl-acetoacetic acid ester, cyclisation 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 offormula I can be used to starting materials for the manufacture of .beta.-lactam antibiotics. The invention relates also to novel intermediates.
565639
Bersier Jacques
Ramos Gerardo
Schneider Peter
Bersier Jacques
Fetherstonhaugh & Co.
Novartis Ag
Ramos Gerardo
Schneider Peter
LandOfFree
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