Process for preparing enol derivatives

There is described a novel process for preparing 7 beta -amino-3- or -2-cephem-3-ol-4-carboxylic acid compounds of the formula IA or of the formula IB where R@ is hydrogen or an amino-protective group R@, R@ is hydrogen or an acyl group Ac, or R@ and R@ together are a bivalent amino-protective group...

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Bibliographic Details
Main Authors ROBERT BURNS WOODWARD, HANS BICKEL
Format Patent
LanguageEnglish
Published 30.10.1981
Subjects
CHEMISTRY
HETEROCYCLIC COMPOUNDS
HUMAN NECESSITIES
HYGIENE
MEDICAL OR VETERINARY SCIENCE
METALLURGY
ORGANIC CHEMISTRY
PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS ORMEDICINAL PREPARATIONS
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Summary:There is described a novel process for preparing 7 beta -amino-3- or -2-cephem-3-ol-4-carboxylic acid compounds of the formula IA or of the formula IB where R@ is hydrogen or an amino-protective group R@, R@ is hydrogen or an acyl group Ac, or R@ and R@ together are a bivalent amino-protective group, R2 is hydroxyl or a radical R@ which together with the carbonyl group -C(=O)- forms a protected carboxyl group, and R3 is hydrogen, lower alkyl or optionally substituted alpha -phenyl(lower alkyl). The process comprises cyclising a 2-[4-(subst.thio)-3-acylamino-2-oxoazetidin-1-yl]-3-subst.amino-croton ic acid compound and solvolysing the 3-amino group in the resulting 7 beta -amino-3-(subst.amino)-3-cephem-4-carboxylic acid intermediate to the -O-R3 group.
Bibliography:Application Number: CH19750002157