A process for the manufacture of 4-acetoxy-3- hydroxy-ethyl-azetidinone

4-Acetoxy-3-hydroxyethylazetidinone of the formula in particular 4(R)-acetoxy-3(R)-(1'(R)-hydroxyethyl)-2-azetidinone, is prepared from enantiomerically pure compounds of the formula in which R denotes lower alkyl and Z denotes amino, arylmethylamino, acylamino or azido, by reduction of the C=C...

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Bibliographische Detailangaben
Hauptverfasser:	SEDELMEIR, GOTTFRIED, BERSIER, JACQUES
Format:	Patent
Sprache:	eng
Schlagworte:	ACYCLIC OR CARBOCYCLIC COMPOUNDS APPARATUS THEREFOR CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOIDCHEMISTRY CHEMISTRY ELECTROLYTIC OR ELECTROPHORETIC PROCESSES ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTIONOF COMPOUNDS OR NON-METALS GENERAL METHODS OF ORGANIC CHEMISTRY HETEROCYCLIC COMPOUNDS METALLURGY ORGANIC CHEMISTRY PERFORMING OPERATIONS PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL THEIR RELEVANT APPARATUS TRANSPORTING
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Beschreibung
Zusammenfassung:	4-Acetoxy-3-hydroxyethylazetidinone of the formula in particular 4(R)-acetoxy-3(R)-(1'(R)-hydroxyethyl)-2-azetidinone, is prepared from enantiomerically pure compounds of the formula in which R denotes lower alkyl and Z denotes amino, arylmethylamino, acylamino or azido, by reduction of the C=C double bond and optionally of the arylmethylamino or azido group with hydrogen, lactone ring opening, ring closure to the beta -lactam, if appropriate after hydrolysis of the acylamino group, and oxidative decarboxylation of the original lactone carboxyl group in the presence of an acetate-releasing agent. Compounds of the formula I can be used as starting substances for the preparation of beta -lactam antibiotics. Novel intermediates and starting materials are also described.