Реакция #42656

Уравнение реакции

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

potassium carbonate

→

title compound

Выход 60.2%

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

Выход 60.2%

Растворители

tetrahydrofuran

methanol

methanol water

Условия реакции

Обработка

1. 1
   Другоеthe solution was partitioned between ethyl acetate and water
2. 2
   Промывкаthe organic layer was washed with water (twice) and brine
3. 3
   Сушкаdried over Na2SO4
4. 4
   ФильтрацияThe solution was filtered
5. 5
   Другоеevaporated in vacuo
6. 6
   Другоеto give an oil which
7. 7
   Другоеwas purified by preparative thin layer chromatography on silica gel
8. 8
   Промывкаeluting with ethyl acetate/hexane/dichloromethane/methanol (3:3:3:1)

Методика

To a solution of (11β,16β)-21-(acetyloxy)-9-fluoro-11-hydroxy-16-methyl-3,20-dioxopregna-1,4-dien-17-yl propylcarbamate (8.5 mg, 0.016 mmol) in 0.3 mL of tetrahydrofuran and 0.1 mL of methanol was added 0.030 mL of a 0.1M solution of potassium carbonate in methanol/water (9:1). After 10 minutes at room temperature, the solution was partitioned between ethyl acetate and water and the organic layer was washed with water (twice) and brine and dried over Na2SO4. The solution was filtered and evaporated in vacuo to give an oil which was purified by preparative thin layer chromatography on silica gel, eluting with ethyl acetate/hexane/dichloromethane/methanol (3:3:3:1), to yield 4.6 mg of the title compound as a semi-solid.

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