반응 #8272

반응 방정식

sodium bicarbonate

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

Potassium carbonate

acetic acid

→

desired product

수율 92.6%

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

수율 92.6%

용매

methanol

반응 조건

후처리

1. 1
   workup.STIRRINGthe mixture stirred for 20 minutes only
2. 2
   기타the methanol evaporated
3. 3
   workup.ADDITIONthe residue diluted with water (100 ml) before extraction of the organics into dichloromethane (250 ml+100 ml)
4. 4
   세척The extract was washed with brine (100 ml)
5. 5
   건조dried (magnesium sulfate)
6. 6
   기타evaporated
7. 7
   기타crude product purified by chromatography on a 300 g silica vacuum sinter column
8. 8
   세척eluting with a gradient from 0% to 20% methanol in dichloromethane

실험 절차

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 (8.64 g, 18 mM) was suspended in methanol (350 ml) and stirred at ambient temperature under nitrogen. Potassium carbonate (3.73 g, 27 mM) was added, and the mixture stirred for 20 minutes only, then neutralised immediately by the addition of acetic acid (2 ml). Saturated aqueous sodium bicarbonate (50 ml) was added, the methanol evaporated, and the residue diluted with water (100 ml) before extraction of the organics into dichloromethane (250 ml+100 ml). The extract was washed with brine (100 ml), dried (magnesium sulfate), evaporated and crude product purified by chromatography on a 300 g silica vacuum sinter column, eluting with a gradient from 0% to 20% methanol in dichloromethane. Relevant fractions were combined to give the desired product (7.3 g).

출처