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

HRID 14377

Reaction equation

HRID 14377 reaction equation
[C:1]1([C@H:7]([NH:9][C:10](=[O:42])[O:11][C@:12]2([C@:36]3([CH3:37])[C@H:22]([C@H:23]4[C@:33]([F:39])([C@@H:34]([OH:38])[CH2:35]3)[C@:31]3([CH3:32])[C:26](=[CH:27][C:28](=[O:40])[CH:29]=[CH:30]3)[CH2:25][CH2:24]4)[CH2:21][C@@H:20]2[CH3:41])[C:13](=[O:19])[CH2:14][O:15]C(=O)C)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CO.C(Cl)(Cl)Cl>[C:1]1([C@H:7]([NH:9][C:10](=[O:42])[O:11][C@:12]2([C@:36]3([CH3:37])[C@H:22]([C@H:23]4[C@:33]([F:39])([C@@H:34]([OH:38])[CH2:35]3)[C@:31]3([CH3:32])[C:26](=[CH:27][C:28](=[O:40])[CH:29]=[CH:30]3)[CH2:25][CH2:24]4)[CH2:21][C@@H:20]2[CH3:41])[C:13](=[O:19])[CH2:14][OH:15])[CH3:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 1

HCID 86603938(11beta,16beta)-21-(acetyloxy)-9-fluoro-11-hydroxy-16-methyl-3,20-dioxopregna-1,4-dien-17-yl (1R)-1-phenylethylcarbamate

Product 1

HCID 44587250(11beta,16beta)-9-Fluoro-11,21-dihydroxy-16-methyl-3,20-dioxopregna-1,4-dien-17-yl (1R)-1-phenylethylcarbamateYield 57.9%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

(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.

Workup

  1. customThe solution was then partitioned between ethyl acetate and water
  2. washthe organic phase was washed with water (twice) and brine
  3. dry with materialdried over Na2SO4
  4. filtrationFiltration and evaporation under vacuum
  5. customgave a white film which
  6. customwas purified by preparative thin layer chromatography on silica gel
  7. washeluting with ethyl acetate/hexane/dichloromethane/methanol (95:95:95:15)

Sources & evidence

ORD record
ord-8bc3ca7a06a94075b52f5ebde43dca6c
Source dataset
uspto-grants-2010_06
Patent number
US07732432B2

Linked notes

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