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

HRID 423277

Reaction equation

HRID 423277 reaction equation
[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]

Participants

6

Reactant 3

HCID 962WaterHCID 23667635Sodium periodateHCID 66676806HCID 66676806, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-c3fd614a0774435a832e2d790d0a555e
Source dataset
uspto-grants-2012_01
Patent number
US08101774B2

Linked notes

Loading…