Hydrogen Peroxide → HCID 66904916, compound

HRID 1692078Notes

Reaction equation

HRID 1692078 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[C:15]([Cl:41])[C:16]=1[CH2:17][C@@H:18]1[CH2:22][CH2:21][N:20]([N:23]2[CH2:28][CH2:27][CH:26]([O:29][Si:30]([CH:37]([CH3:39])[CH3:38])([CH:34]([CH3:36])[CH3:35])[CH:31]([CH3:33])[CH3:32])[CH2:25][CH2:24]2)[C:19]1=[O:40])[O:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1.C(=O)([O-])[O-:43].[K+].[K+].OO.C(OCC)(=O)C>CS(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[C:15]([Cl:41])[C:16]=1[CH2:17][C@@H:18]1[CH2:22][CH2:21][N:20]([N:23]2[CH2:24][CH2:25][CH:26]([O:29][Si:30]([CH:34]([CH3:35])[CH3:36])([CH:37]([CH3:39])[CH3:38])[CH:31]([CH3:32])[CH3:33])[CH2:27][CH2:28]2)[C:19]1=[O:40])[O:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]([NH2:11])=[O:43])=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 66905082HCID 66905082, compound

Product 1

HCID 66904916HCID 66904916, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Cool a solution of (R)-4-{3,5-dichloro-4-[2-oxo-1-(4-triisopropylsilanyloxy-piperidin-1-yl)-pyrrolidin-3-ylmethyl]-phenoxy}-benzonitrile (0.295 g, 0.48 mmol) in DMSO (5 mL) on an ice bath. Add to the solution potassium carbonate (0.331 g, 2.4 mmol) and hydrogen peroxide (30% in water, 1 mL) and stir the reaction at 0° C. for 1.5 hours and then at room temperature for 12 hours. Dilute the reaction with ethyl acetate, and wash three times with water and then one time with brine. Dry the organic phase over sodium sulfate, filter, and concentrate. Purify the residue by silica gel chromatography by eluting with 40% ethyl acetate in hexanes to 100% ethyl acetate gradient to afford 0.210 g (69%) of the title compound. MS (m/z): 633 (M+).

Workup

  1. customthe reaction at 0° C. for 1.5 hours
  2. additionDilute
  3. washwash three times with water
  4. dry with materialDry the organic phase over sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify the residue by silica gel chromatography
  8. washby eluting with 40% ethyl acetate in hexanes to 100% ethyl acetate gradient

Sources & evidence

ORD record
ord-42416b3c15e14967b31d36ae3c900ad2
Source dataset
uspto-grants-2012_04
Patent number
US08153807B2

Reaction notes

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