Hydrogen Peroxide → HCID 131735376, compound

HRID 629482Notes

Reaction equation

HRID 629482 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH2:10][C:11]1[CH:12]=[C:13]2[C:17](=[C:18]([CH3:21])[C:19]=1[CH3:20])[CH2:16][N:15]([C@H:22]1[C@H:27]([OH:28])[CH2:26][CH2:25][O:24][CH2:23]1)[C:14]2=[O:29])[C:5]#[N:6].C(=O)([O-])[O-:31].[K+].[K+].OO>CS(C)=O.O>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH2:10][C:11]1[CH:12]=[C:13]2[C:17](=[C:18]([CH3:21])[C:19]=1[CH3:20])[CH2:16][N:15]([C@H:22]1[C@H:27]([OH:28])[CH2:26][CH2:25][O:24][CH2:23]1)[C:14]2=[O:29])[C:5]([NH2:6])=[O:31]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 130422883HCID 130422883, compound

Product 1

HCID 131735376HCID 131735376, compoundYield 83.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a mixture of rac-3-fluoro-4-((2-(trans-4-hydroxytetrahydro-2H-pyran-3-yl)-6,7-dimethyl-3-oxoisoindolin-5-yl)methyl)benzonitrile (0.08 g) and potassium carbonate (0.08 g) in DMSO (2.00 mL) was added 35% aqueous hydrogen peroxide (0.17 mL) under ice-cooling, and the mixture was stirred at room temperature for 3 hr. The reaction solution was diluted with water, and the mixture was extracted with ethyl acetate-THF. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was washed with ethyl acetate to give the title compound (0.07 g).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate-THF
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. washThe residue was washed with ethyl acetate

Sources & evidence

ORD record
ord-26c6ca77c5fe4497b1b59555e1628e49
Source dataset
uspto-grants-2016_04
Patent number
US09315458B2

Reaction notes

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