Reaktion #42656

Reaktionsgleichung

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

potassium carbonate

→

title compound

Ausbeute 60.2%

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

Ausbeute 60.2%

Lösungsmittel

tetrahydrofuran

methanol

methanol water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe solution was partitioned between ethyl acetate and water
2. 2
   Waschenthe organic layer was washed with water (twice) and brine
3. 3
   Trocknendried over Na2SO4
4. 4
   FiltrationThe solution was filtered
5. 5
   Sonstigeevaporated in vacuo
6. 6
   Sonstigeto give an oil which
7. 7
   Sonstigewas purified by preparative thin layer chromatography on silica gel
8. 8
   Wascheneluting with ethyl acetate/hexane/dichloromethane/methanol (3:3:3:1)

Vorschrift

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.

Quelle