Boron trifluoride etherate → (11beta,16beta)-21-(Acetyloxy)-9-fluoro-11-hydroxy-16-methyl-3,20-dioxopregna-1,4-dien-17-yl ethylcarbamate

HRID 14376ノート

反応式

HRID 14376 の反応式
[CH2:1]([NH:3][C:4](=[O:40])[O:5][C@:6]1([C@:30]2([CH3:31])[C@H:16]([C@H:17]3[C@:27]([F:37])([C@@H:28]([O:32][Si](C)(C)C)[CH2:29]2)[C@:25]2([CH3:26])[C:20](=[CH:21][C:22](=[O:38])[CH:23]=[CH:24]2)[CH2:19][CH2:18]3)[CH2:15][C@@H:14]1[CH3:39])[C:7](=[O:13])[CH2:8][O:9][C:10](=[O:12])[CH3:11])[CH3:2].B(F)(F)F.CCOCC.CCCCCC.C(OCC)(=O)C.ClCCl.CO>C(#N)C>[CH2:1]([NH:3][C:4](=[O:40])[O:5][C@:6]1([C@:30]2([CH3:31])[C@H:16]([C@H:17]3[C@:27]([F:37])([C@@H:28]([OH:32])[CH2:29]2)[C@:25]2([CH3:26])[C:20](=[CH:21][C:22](=[O:38])[CH:23]=[CH:24]2)[CH2:19][CH2:18]3)[CH2:15][C@@H:14]1[CH3:39])[C:7](=[O:13])[CH2:8][O:9][C:10](=[O:12])[CH3:11])[CH3:2]

参加物

5

反応物 3

HCID 8000Boron trifluoride etherate2 回HCID 23322409Hexane ethyl acetate dichloromethane methanolHCID 68717367(11beta,16beta)-21-(Acetyloxy)-9-fluoro-16-methyl-3,20-dioxo-11-[(trimethylsilyl)-oxy]pregna-1,4-dien-17-yl ethylcarbamate

生成物 1

HCID 58613239(11beta,16beta)-21-(Acetyloxy)-9-fluoro-11-hydroxy-16-methyl-3,20-dioxopregna-1,4-dien-17-yl ethylcarbamate

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a solution of (11β,16β)-21-(acetyloxy)-9-fluoro-16-methyl-3,20-dioxo-11-[(trimethylsilyl)-oxy]pregna-1,4-dien-17-yl ethylcarbamate (138 mg, 0.239 mmol) in 2.5 mL of acetonitrile was added boron trifluoride etherate (0.12 mL, 0.96 mmol). After stirring at room temperature for 5 hours, additional boron trifluoride etherate (0.060 mL, 0.47 mmol) was added. The solution was stirred at room temperature for 15 hours more and was then partitioned between ethyl acetate and water. The organic layer was washed with water (twice) and brine and dried over Na2SO4. Filtration and evaporation under vacuum gave a pale yellow oil. Chromatography on silica gel eluting with hexane/ethyl acetate/dichloromethane/methanol (5:2:2:1) gave (11β,16β)-21-(acetyloxy)-9-fluoro-11-hydroxy-16-methyl-3,20-dioxopregna-1,4-dien-17-yl ethylcarbamate as a white film.

後処理

  1. stirringThe solution was stirred at room temperature for 15 hours more
  2. customwas then partitioned between ethyl acetate and water
  3. washThe organic layer was washed with water (twice) and brine
  4. dry with materialdried over Na2SO4
  5. filtrationFiltration and evaporation under vacuum
  6. customgave a pale yellow oil

出典と根拠

ORDレコード
ord-6c8ca8acc3fc44e5bba58e173c85907f
出典データセット
uspto-grants-2010_06
特許番号
US07732432B2

反応ノート

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