Sodium Hydroxide → 1-{[(5-{3-fluoro-4-[4-(trifluoromethyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl]phenyl}-4-methylpyridin-2-yl)oxy]methyl}cyclobutanecarboxylic acid

HRID 623913노트

반응식

HRID 623913 반응식
[OH-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([C:27]2[C:28]([CH3:44])=[CH:29][C:30]([O:33][CH2:34][C:35]3([C:39]([O:41]CC)=[O:40])[CH2:38][CH2:37][CH2:36]3)=[N:31][CH:32]=2)[CH:7]=[CH:8][C:9]=1[C:10]1[N:11]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[N:14]=1>CO>[F:3][C:4]1[CH:5]=[C:6]([C:27]2[C:28]([CH3:44])=[CH:29][C:30]([O:33][CH2:34][C:35]3([C:39]([OH:41])=[O:40])[CH2:36][CH2:37][CH2:38]3)=[N:31][CH:32]=2)[CH:7]=[CH:8][C:9]=1[C:10]1[N:11]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[CH:12]=[C:13]([C:15]([F:18])([F:16])[F:17])[N:14]=1

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 86698178ethyl 1-{[(5-{3-fluoro-4-[4-(trifluoromethyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl]phenyl}-4-methylpyridin-2-yl)oxy]methyl}cyclobutanecarboxylate

생성물 1

HCID 679753231-{[(5-{3-fluoro-4-[4-(trifluoromethyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl]phenyl}-4-methylpyridin-2-yl)oxy]methyl}cyclobutanecarboxylic acid수율 102.5%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Methanol (6.3 mL) and 1N aqueous sodium hydroxide solution (2.6 mL) were added to ethyl 1-{[(5-{3-fluoro-4-[4-(trifluoromethyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl]phenyl}-4-methylpyridin-2-yl)oxy]methyl}cyclobutanecarboxylate (315 mg) and the mixture was refluxed for 1 hour. Methanol was distilled off under reduced pressure, and the residue was neutralized by 1N hydrochloric acid. The mixture was extracted with ethyl acetate, the organic layer was washed with a saturated brine, and dried over anhydrous magnesium sulfate. After concentrating the mixture under reduced pressure, the obtained residue was purified by silica gel column chromatography (chloroform:methanol=100:0 to 95:5) to obtain 1-{[(5-{3-fluoro-4-[4-(trifluoromethyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl]phenyl}-4-methylpyridin-2-yl)oxy]methyl}cyclobutanecarboxylic acid (308 mg).

후처리

  1. temperaturethe mixture was refluxed for 1 hour
  2. distillationMethanol was distilled off under reduced pressure
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe organic layer was washed with a saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationAfter concentrating the mixture under reduced pressure
  7. customthe obtained residue was purified by silica gel column chromatography (chloroform:methanol=100:0 to 95:5)

출처 및 근거

ORD 기록
ord-c5699545a8fb46f19d58bd004d1150ec
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09302996B2

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