Asymmetric process for preparing antibiotics being selected from a group comprising florfenicol, thiamphenicol and chloramphenicol

The invented process comprises regioselective opening of a chiral epoxide of the general formula IV by successive treatment with a strong base, a Lewis acid and dichloroacetonitrile under formation of a chiral epoxide of the general formula V and subsequent stereoselective inversion/isomerization th...

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Bibliographic Details
Main Authors WU GUANG-ZHONG, TORMOS WANDA I
Format Patent
LanguageEnglish
Published 15.11.2000
Edition7
Subjects
ACYCLIC OR CARBOCYCLIC COMPOUNDS
APPARATUS THEREFOR
CHEMISTRY
GENERAL METHODS OF ORGANIC CHEMISTRY
HETEROCYCLIC COMPOUNDS
HUMAN NECESSITIES
HYGIENE
MEDICAL OR VETERINARY SCIENCE
METALLURGY
ORGANIC CHEMISTRY
PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
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Summary:The invented process comprises regioselective opening of a chiral epoxide of the general formula IV by successive treatment with a strong base, a Lewis acid and dichloroacetonitrile under formation of a chiral epoxide of the general formula V and subsequent stereoselective inversion/isomerization thereof to oxazoline of the general formula VI, whereby R represents in all the formulae methane sulfonyl or a nitro group. Oxazoline of the general formula VI, wherein R represents methane sulfonyl is subjected either to fluorination and subsequent hydrolysis under formation of florfenicol of the general formula I, or the oxazoline of the general formula VI, wherein R represents a nitro group or methane sulfonyl is subjected to hydrolysis under formation of thiamphenicol or chloramphenicol.
Bibliography:Application Number: CZ19950001598