(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

反応式

HRID 14377 の反応式
[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

参加物

3

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 21584188Chloroform methanol溶媒

実験手順

(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.

後処理

  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)

出典と根拠

ORDレコード
ord-8bc3ca7a06a94075b52f5ebde43dca6c
出典データセット
uspto-grants-2010_06
特許番号
US07732432B2

関連ノート

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