반응 #8271

반응 방정식

sodium bicarbonate

3-(4-(1,2,5,6-tetrahydropyridyl)-3,5-difluorophenyl)-5(R)-acetoxymethyloxazolidin-2-one hydrochloride

pyridine

2,2-dimethyl-1,3-dioxolan-4(S)-ylcarbonyl chloride

→

title compound

수율 97.7%

3-(4(1-(2,2-Dimethyl-1,3-dioxolan-4(S)-ylcarbonyl)-1,2,5,6-tetrahydropyrid-4-yl)-3,5-difluorophenyl)-5(R)-acetoxymethyloxazolidin-2-one

수율 97.7%

용매

dichloromethane

dichloromethane

반응 조건

후처리

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITcontinued for 30 minutes
3. 3
   기타The organic phase was separated
4. 4
   건조dried (magnesium sulfate)
5. 5
   여과filtered
6. 6
   기타evaporated to dryness
7. 7
   workup.ADDITIONafter the addition of toluene (20 ml)
8. 8
   기타The solid residue was triturated with a mixture of diethyl ether (250 ml) and isohexane (150 ml), and solid
9. 9
   여과filtered

실험 절차

3-(4-(1,2,5,6-tetrahydropyridyl)-3,5-difluorophenyl)-5(R)-acetoxymethyloxazolidin-2-one hydrochloride (14.5 g, 37.3 mM) was suspended in dry dichloromethane (300 ml) under nitrogen at 0°, and treated with pyridine (9.78 g, 0.12 M). A solution of 2,2-dimethyl-1,3-dioxolan-4(S)-ylcarbonyl chloride (9.59 g, 75.6 mM) in dichloromethane (100 ml) was added dropwise, and stirring continued for 3 hours, allowing the temperature to rise to ambient. Aqueous sodium bicarbonate (5%, 300 ml) was added, and stirring continued for 30 minutes. The organic phase was separated, dried (magnesium sulfate), filtered, and evaporated to dryness after the addition of toluene (20 ml). The solid residue was triturated with a mixture of diethyl ether (250 ml) and isohexane (150 ml), and solid filtered to give the title compound (17.5 g).

출처