Hydrogen Peroxide → HCID 66634234, compound

HRID 563835Notes

Reaction equation

HRID 563835 reaction equation
[C:1]([CH2:3][C:4]1[CH:5]=[CH:6][C:7]([O:29][CH3:30])=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:11]=2[CH2:20][N:21]([CH2:27][CH3:28])[C:22]([CH:24]2[CH2:26][CH2:25]2)=[O:23])[CH:9]=1)#[N:2].C(=O)([O-])[O-:32].[K+].[K+].OO>CS(C)=O>[C:1]([CH2:3][C:4]1[CH:5]=[CH:6][C:7]([O:29][CH3:30])=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:18])([F:19])[F:17])=[CH:12][C:11]=2[CH2:20][N:21]([CH2:27][CH3:28])[C:22]([CH:24]2[CH2:25][CH2:26]2)=[O:23])[CH:9]=1)(=[O:32])[NH2:2]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 66606761HCID 66606761, compound

Product 1

HCID 66634234HCID 66634234, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of cyclopropanecarboxylic acid (5′-cyanomethyl-2′-methoxy-4-trifluoromethyl-biphenyl-2-ylmethyl)-ethyl-amide (0.064 g, 0.15 mmol) and potassium carbonate (0.064 g, 0.46 mmol) in DMSO (1 mL) at 0° C. was added hydrogen peroxide (30%; 0.44 mL), and the reaction was warmed to room temperature and stirred for 3 hours. The mixture was partitioned between EtOAc and aqueous Na2S2O4, and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated to give the title compound. M+H is 435.

Workup

  1. customThe mixture was partitioned between EtOAc and aqueous Na2S2O4
  2. extractionthe aqueous layer was extracted with EtOAc
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-226c6aae363a4950ab003ea50357f38e
Source dataset
uspto-grants-2011_11
Patent number
US08067445B2

Reaction notes

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