반응 #464266

반응 방정식

dichloromethane

(4aS,6S,7R,7aR)-6,7-epoxy-1,4a,5,6,7,7a-hexahydro-1-hydroxy-7-methylcyclopenta[c]pyrane-4-carboxylic acid methylester

chloroacetylisocyanate

→

(1R,4aS,6S,7R,7aR)-1-(chloroacetylcarbamoyloxy)-6,7-epoxy-1,4a,5,6,7,7a-hexahydro-7-methylcyclopenta[c]pyrane-4-carboxylic acid methylester

수율 91.0%

용매

hexane ethyl acetate

반응 조건

후처리

1. 1
   온도was cooled with ice
2. 2
   추출The reaction mixture was then extracted with dichloromethane
3. 3
   세척After washing the organic phase with brine, it
4. 4
   건조was dried over anhydrous magnesium sulfate
5. 5
   workup.DISTILLATIONAfter distilling off the solvent under reduced pressure
6. 6
   기타the residue was purified by silica gel chromatography

실험 절차

A dichloromethane solution containing 100 mg of a known (4aS,6S,7R,7aR)-6,7-epoxy-1,4a,5,6,7,7a-hexahydro-1-hydroxy-7-methylcyclopenta[c]pyrane-4-carboxylic acid methylester was cooled with ice followed by addition of chloroacetylisocyanate (45 ml) and stirring for 15 hours at room temperature. The reaction mixture was then extracted with dichloromethane. After washing the organic phase with brine, it was dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel chromatography to obtain a colorless powder from the hexane-ethyl acetate eluate in the form of (1R,4aS,6S,7R,7aR)-1-(chloroacetylcarbamoyloxy)-6,7-epoxy-1,4a,5,6,7,7a-hexahydro-7-methylcyclopenta[c]pyrane-4-carboxylic acid methylester (137 mg, yield: 91%). The physicochemical properties of this compound are described in Table 8, Compound No. 40.

출처