Sodium Thiosulfate → Methyl 4-((1-(4-((3,3-dimethyl-2-oxobutyl)carbamoyl)-2-methylphenyl)-4,4,4-trifluorobutyl)amino)benzoate

HRID 1520287Notes

Reaction equation

HRID 1520287 reaction equation
[F:1][C:2]([F:35])([F:34])[CH2:3][CH2:4][CH:5]([NH:23][C:24]1[CH:33]=[CH:32][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][CH:25]=1)[C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:21])[NH:13][CH2:14][CH:15]([OH:20])[C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:8][C:7]=1[CH3:22].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)([O-])O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(OCC)(=O)C>[CH3:17][C:16]([CH3:19])([CH3:18])[C:15](=[O:20])[CH2:14][NH:13][C:12]([C:9]1[CH:10]=[CH:11][C:6]([CH:5]([NH:23][C:24]2[CH:25]=[CH:26][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:32][CH:33]=2)[CH2:4][CH2:3][C:2]([F:35])([F:34])[F:1])=[C:7]([CH3:22])[CH:8]=1)=[O:21]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 117840033Methyl 4-((4,4,4-trifluoro-1-(4-((2-hydroxy-3,3-dimethylbutyl)carbamoyl)-2-methylphenyl)butyl)amino)benzoate

Product 1

HCID 117840039Methyl 4-((1-(4-((3,3-dimethyl-2-oxobutyl)carbamoyl)-2-methylphenyl)-4,4,4-trifluorobutyl)amino)benzoateYield 90.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of methyl 4-((4,4,4-trifluoro-1-(4-((2-hydroxy-3,3-dimethylbutyl)carbamoyl)-2-methylphenyl)butyl)amino)benzoate (479.1 mg) and ethyl acetate (10 mL) was added Dess-Martin Periodinane (616 mg) at room temperature, and the mixture was stirred overnight. To the reaction mixture were added saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium thiosulfate solution, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (433.8 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-409a56037b754b69a153495dcc0a3bf3
Source dataset
uspto-grants-2015_07
Patent number
US09073864B2

Reaction notes

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