Hydrogen Peroxide → HCID 57741478, compound

HRID 416006Notes

Reaction equation

HRID 416006 reaction equation
C(=O)([O-])[O-:2].[K+].[K+].OO.[Cl:9][C:10]1[CH:11]=[C:12]([C:30]2[CH:35]=[CH:34][C:33]([C:36]#[N:37])=[C:32]([F:38])[CH:31]=2)[CH:13]=[C:14]([Cl:29])[C:15]=1[CH2:16][CH:17]1[CH2:21][CH2:20][N:19]([CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[C:18]1=[O:28]>CS(C)=O>[Cl:9][C:10]1[CH:11]=[C:12]([C:30]2[CH:35]=[CH:34][C:33]([C:36]([NH2:37])=[O:2])=[C:32]([F:38])[CH:31]=2)[CH:13]=[C:14]([Cl:29])[C:15]=1[CH2:16][CH:17]1[CH2:21][CH2:20][N:19]([CH:22]2[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]2)[C:18]1=[O:28]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 66621782HCID 66621782, compound

Product 1

HCID 57741478HCID 57741478, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Add potassium carbonate (83 mg, 0.6 mmol) and hydrogen peroxide (30% in water, 0.5 mL) to a solution of Preparation 13 (3′,5′-dichloro-4′-(1-cyclohexyl-2-oxo-pyrrolidin-3-ylmethyl)-3-fluoro-biphenyl-4-carbonitrile) (88 mg, 0.2 mmol) in DMSO (3 mL). Stir the reaction at room temperature for 12 h. Partition the mixture between ethyl acetate (20 mL) and water (20 mL). Separate the organic layer, wash three times with water (15 mL each) then brine (15 mL). After drying the organic layer over sodium sulfate, filter and concentrate under vacuum. Purify the residue by silica gel chromatography with 1:1 ethyl acetate/hexane to afford the title compound: MS (m/z): 463 (M+).

Workup

  1. customthe reaction at room temperature for 12 h
  2. customPartition the mixture between ethyl acetate (20 mL) and water (20 mL)
  3. customSeparate the organic layer
  4. washwash three times with water (15 mL each)
  5. dry with materialAfter drying the organic layer over sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate under vacuum
  8. customPurify the residue by silica gel chromatography with 1:1 ethyl acetate/hexane

Sources & evidence

ORD record
ord-620f83bd0fee41e98fadd585e240045e
Source dataset
uspto-grants-2012_01
Patent number
US08088776B2

Reaction notes

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