反応 #8263

反応方程式

3-(4-(3(S)-Aminopyrrolidin-1-yl)-3-fluorophenyl)-5(R)-(N-(2,2,2-trichloroethyl-oxycarbonyl)isoxazol-3-ylaminomethyl)oxazolidin-2-one hydrochloride salt

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

→

desired product

収率 143.5%

3-(4-(3(S)-(2(S),3-Dihydroxypropanoyl)pyrrolidin-1-yl)-3-fluorophenyl)-5(S)-(isoxazol-3-ylaminomethyl)oxazolidin-2-one

収率 143.5%

溶媒

pyridine

dichloromethane

ethyl acetate

water

反応条件

後処理

1. 1
   その他the organic layer separated
2. 2
   洗浄washed with aqueous sodium bicarbonate (10 ml) and brine (10 ml)
3. 3
   その他evaporated
4. 4
   その他azeotroped with toluene (20 ml)
5. 5
   その他The residue was purified by chromatography on a 10 g silica Mega Bond Elut® column
6. 6
   洗浄eluting with
7. 7
   温度a gradient increasing in polarity from 0 to 100% ethyl acetate in dichloromethane
8. 8
   その他evaporated

実験手順

3-(4-(3(S)-Aminopyrrolidin-1-yl)-3-fluorophenyl)-5(R)-(N-(2,2,2-trichloroethyl-oxycarbonyl)isoxazol-3-ylaminomethyl)oxazolidin-2-one hydrochloride salt (400 mg, 0.698 mM) in pyridine (5 ml) was treated dropwise with a solution of 2,2-dimethyl-1,3-dioxolan-4(S)-ylcarbonyl chloride (200 mg, 1.2 mM) in dichloromethane (2 ml), and the mixture stirred 3 hours at ambient temperature. The mixture was diluted with ethyl acetate (15 ml) and water (15 ml), the organic layer separated, washed with aqueous sodium bicarbonate (10 ml) and brine (10 ml), and evaporated, then azeotroped with toluene (20 ml). The residue was purified by chromatography on a 10 g silica Mega Bond Elut® column, eluting with a gradient increasing in polarity from 0 to 100% ethyl acetate in dichloromethane. Relevant fractions were combined and evaporated to give the desired product (435 mg).

出典