Реакция #42655

Уравнение реакции

(11β,16β)-21-(acetyloxy)-9-fluoro-11-hydroxy-16-methyl-3,20-dioxopregna-1,4-dien-17-yl (1R)-1-phenylethylcarbamate

→

(11β,16β)-9-fluoro-11,21-dihydroxy-16-methyl-3,20-dioxopregna-1,4-dien-17-yl (1R)-1-phenylethylcarbamate

Выход 57.9%

Растворители

—

pre-mixed solution

methanol chloroform

Условия реакции

Обработка

1. 1
   ДругоеThe solution was then partitioned between ethyl acetate and water
2. 2
   Промывкаthe organic phase was washed with water (twice) and brine
3. 3
   Сушкаdried over Na2SO4
4. 4
   ФильтрацияFiltration and evaporation under vacuum
5. 5
   Другоеgave a white film which
6. 6
   Другоеwas purified by preparative thin layer chromatography on silica gel
7. 7
   Промывкаeluting with ethyl acetate/hexane/dichloromethane/methanol (95:95:95:15)

Методика

(11β,16β)-21-(acetyloxy)-9-fluoro-11-hydroxy-16-methyl-3,20-dioxopregna-1,4-dien-17-yl (1R)-1-phenylethylcarbamate (42 mg, 0.064 mmol) was dissolved in 1.25 mL of a pre-mixed solution of methanol/chloroform/6N HCl (10:2:1) and stirred at room temperature for 24.5 hours. The solution was then partitioned between ethyl acetate and water and the organic phase was washed with water (twice) and brine and dried over Na2SO4. Filtration and evaporation under vacuum gave a white film which was purified by preparative thin layer chromatography on silica gel, eluting with ethyl acetate/hexane/dichloromethane/methanol (95:95:95:15), to yield 20 mg of (11β,16β)-9-fluoro-11,21-dihydroxy-16-methyl-3,20-dioxopregna-1,4-dien-17-yl (1R)-1-phenylethylcarbamate as a white solid.

Источник