반응 #42655

반응 방정식

(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

수율 57.9%

용매

—

pre-mixed solution

methanol chloroform

반응 조건

후처리

1. 1
   기타The solution was then partitioned between ethyl acetate and water
2. 2
   세척the organic phase was washed with water (twice) and brine
3. 3
   건조dried over Na2SO4
4. 4
   여과Filtration and evaporation under vacuum
5. 5
   기타gave a white film which
6. 6
   기타was purified by preparative thin layer chromatography on silica gel
7. 7
   세척eluting with ethyl acetate/hexane/dichloromethane/methanol (95:95:95:15)

실험 절차

(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.

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