반응 #8263

반응 방정식

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

수율 143.5%

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

수율 143.5%

용매

pyridine

dichloromethane

ethyl acetate

water

반응 조건

후처리

1. 1
   기타the organic layer separated
2. 2
   세척washed with aqueous sodium bicarbonate (10 ml) and brine (10 ml)
3. 3
   기타evaporated
4. 4
   기타azeotroped with toluene (20 ml)
5. 5
   기타The residue was purified by chromatography on a 10 g silica Mega Bond Elut® column
6. 6
   세척eluting with
7. 7
   온도a gradient increasing in polarity from 0 to 100% ethyl acetate in dichloromethane
8. 8
   기타evaporated

실험 절차

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).

출처