Water → 4'-Trifluoromethylbiphenyl-2-carboxylic acid (2-dimethylcarbamoyl-4-formylphenyl)amide

HRID 423277

반응식

HRID 423277 반응식
[CH3:1][N:2]([CH3:32])[C:3]([C:5]1[CH:10]=[C:9]([CH:11]=C)[CH:8]=[CH:7][C:6]=1[NH:13][C:14]([C:16]1[C:17]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=2)=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:15])=[O:4].O.I([O-])(=O)(=O)=[O:35].[Na+]>CC(C)=O.[Os](=O)(=O)(=O)=O>[CH3:32][N:2]([CH3:1])[C:3]([C:5]1[CH:10]=[C:9]([CH:11]=[O:35])[CH:8]=[CH:7][C:6]=1[NH:13][C:14]([C:16]1[C:17]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:29])[F:30])=[CH:24][CH:23]=2)=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:15])=[O:4]

참가 물질

6

반응물 3

HCID 962WaterHCID 23667635Sodium periodateHCID 66676806HCID 66676806, 화합물

생성물 1

HCID 866046484'-Trifluoromethylbiphenyl-2-carboxylic acid (2-dimethylcarbamoyl-4-formylphenyl)amide수율 73.3%

시약·촉매·용매 2

HCID 30318Osmium Tetroxide촉매HCID 180Acetone용매

실험 절차

To a mixed solution of 4′-trifluoromethylbiphenyl-2-carboxylic acid (2-dimethylcarbamoyl-4-vinylphenyl)amide (774 mg) in acetone (10 mL)-water (10 mL) were added osmium tetroxide (10% (w/w) microcapsule; 449 mg) and sodium metaperiodate (944 mg). The mixture was stirred at room temperature for 4 hours and filtered through a Celite pad. The filtrate was concentrated in vacuo. The residue was diluted with ethyl acetate, washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:2, v/v) to give the title compound (570 mg).

후처리

  1. filtrationfiltered through a Celite pad
  2. concentrationThe filtrate was concentrated in vacuo
  3. additionThe residue was diluted with ethyl acetate
  4. washwashed successively with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:2, v/v)

출처 및 근거

ORD 기록
ord-c3fd614a0774435a832e2d790d0a555e
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101774B2

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