Реакция #8263

Уравнение реакции

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

Выход 143.5%

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

Выход 143.5%

Растворители

pyridine

dichloromethane

ethyl acetate

water

Условия реакции

Обработка

1. 1
   Другоеthe organic layer separated
2. 2
   Промывкаwashed with aqueous sodium bicarbonate (10 ml) and brine (10 ml)
3. 3
   Другоеevaporated
4. 4
   Другоеazeotroped with toluene (20 ml)
5. 5
   ДругоеThe residue was purified by chromatography on a 10 g silica Mega Bond Elut® column
6. 6
   Промывкаeluting with
7. 7
   Температураa gradient increasing in polarity from 0 to 100% ethyl acetate in dichloromethane
8. 8
   Другоеevaporated

Методика

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).

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