Réaction #42656

Équation de réaction

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

potassium carbonate

→

title compound

Rendement 60.2%

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

Rendement 60.2%

Solvants

tetrahydrofuran

methanol

methanol water

Conditions de réaction

Traitement

1. 1
   Autrethe solution was partitioned between ethyl acetate and water
2. 2
   Lavagethe organic layer was washed with water (twice) and brine
3. 3
   Séchagedried over Na2SO4
4. 4
   FiltrationThe solution was filtered
5. 5
   Autreevaporated in vacuo
6. 6
   Autreto give an oil which
7. 7
   Autrewas purified by preparative thin layer chromatography on silica gel
8. 8
   Lavageeluting with ethyl acetate/hexane/dichloromethane/methanol (3:3:3:1)

Mode opératoire

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.

Source