反応 #8272

反応方程式

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

収率 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

収率 92.6%

溶媒

methanol

反応条件

後処理

1. 1
   workup.STIRRINGthe mixture stirred for 20 minutes only
2. 2
   その他the 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
   洗浄The extract was washed with brine (100 ml)
5. 5
   乾燥dried (magnesium sulfate)
6. 6
   その他evaporated
7. 7
   その他crude product purified by chromatography on a 300 g silica vacuum sinter column
8. 8
   洗浄eluting with a gradient from 0% to 20% methanol in dichloromethane

実験手順

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).

出典