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

HRID 14376노트

반응식

HRID 14376 반응식
[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]

참가 물질

5

반응물 3

HCID 8000Boron trifluoride etherate2회HCID 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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6c8ca8acc3fc44e5bba58e173c85907f
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732432B2

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