PROCESS FOR THE MANUFACTURE OF 4-ACYLOXY-3-HYDROXYETHY L-AZETIDINONES

PROCESS FOR THE MANUFACTURE OF 4-ACYLOXY-3-HYDROXYETHY L-AZETIDINONES

The invention relates to a novel process for the manufacture of (3R,1'R)4-acyloxy-3-(1'-hydroxyethyl)-2-azetidinones of formula (I) in which R1 represents lower alkyl or aryl, by enantioselective reduction of the carbonyl group in a suitable .alpha.-acylaminomethyl-acetoacetic acid ester,...

Ausführliche Beschreibung

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Bibliographische Detailangaben
Hauptverfasser: SCHNEIDER, PETER, BERSIER, JACQUES, RAMOS, GERARDO
Format: Patent
Sprache:eng ; fre
Schlagworte:
ACYCLIC OR CARBOCYCLIC COMPOUNDS
APPARATUS THEREFOR
BEER
BIOCHEMISTRY
CHEMISTRY
ELECTROLYTIC OR ELECTROPHORETIC PROCESSES
ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTIONOF COMPOUNDS OR NON-METALS
ENZYMOLOGY
FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIREDCHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERSFROM A RACEMIC MIXTURE
HETEROCYCLIC COMPOUNDS
METALLURGY
MICROBIOLOGY
MUTATION OR GENETIC ENGINEERING
ORGANIC CHEMISTRY
SPIRITS
VINEGAR
WINE
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Beschreibung
Zusammenfassung:The invention relates to a novel process for the manufacture of (3R,1'R)4-acyloxy-3-(1'-hydroxyethyl)-2-azetidinones of formula (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.-hydroxybutyri c 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.