OPTICALLY ACTIVE IMIDAZOLYLMETHYLOXIRANE DERIVATIVE AND ITS PREPARATION

OPTICALLY ACTIVE IMIDAZOLYLMETHYLOXIRANE DERIVATIVE AND ITS PREPARATION

NEW MATERIAL:(R)-2-(2,4-Dichlorophenyl)-2-(imidazol-1-yl)methyloxirane of formula I . USE:A synthetic intermediate of optically active imidazolylalkylthiopropanol derivative having strong antifungal activity. PROCESS:The racemic isomer of the imidazolyldiol derivative of formula II is made to react...

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Bibliographische Detailangaben
Hauptverfasser: ICHINOSE KATSUAKI, AONO SHIYUNJI, OKUDA TAKAO, ATAMI TOSHIO, SAJI KITAROU, SATOU RENZOU
Format: Patent
Sprache:eng
Schlagworte:
ACYCLIC OR CARBOCYCLIC COMPOUNDS
APPARATUS THEREFOR
CHEMISTRY
GENERAL METHODS OF ORGANIC CHEMISTRY
HETEROCYCLIC COMPOUNDS
METALLURGY
ORGANIC CHEMISTRY
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Zusammenfassung:NEW MATERIAL:(R)-2-(2,4-Dichlorophenyl)-2-(imidazol-1-yl)methyloxirane of formula I . USE:A synthetic intermediate of optically active imidazolylalkylthiopropanol derivative having strong antifungal activity. PROCESS:The racemic isomer of the imidazolyldiol derivative of formula II is made to react with an optically active carboxylic acid (or its reactive derivative) (preferably the compound of formula III) to obtain two kinds of diastereomer esters, from which the objective ester is separated. The separated ester is hydrolyzed under alkaline condition, and the resultant optically active imidazolyldiol derivative of formula IV is methylated with methanesulfonyl chloride, and without isolating from the reaction system, treated with an alkali to obtain the objective compound of formula I .