Hydrogen Peroxide → HCID 67404491, compound

HRID 906197Notes

Reaction equation

HRID 906197 reaction equation
[C:1]([C:3]1[C:12]([NH:13][CH:14]([CH2:17][CH3:18])[CH2:15][CH3:16])=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([C:19]([F:22])([F:21])[F:20])[CH:4]=1)#[N:2].OO.C(=O)([O-])[O-:26].[K+].[K+]>CS(C)=O>[NH2:2][C:1]([C:3]1[C:12]([NH:13][CH:14]([CH2:17][CH3:18])[CH2:15][CH3:16])=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([C:19]([F:21])([F:20])[F:22])[CH:4]=1)=[O:26]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 67401806HCID 67401806, compound

Product 1

HCID 67404491HCID 67404491, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Methyl 4-cyano-5-(pentan-3-ylamino)-2-(trifluoromethyl)benzoate (257 mg, 0.818 mmol) was dissolved in DMSO (2 mL) and was cooled in a cold water bath. 30% Aqueous hydrogen peroxide (0.2 mL) and potassium carbonate (38 mg, 0.275 mmol) was added and the mixture was stirred at ambient temperature for 1.5 h. The reaction mixture was partitioned between ethyl acetate and water. The aqueous portion was extracted with ethyl acetate. The combined organic portion was dried over sodium sulfate then filtered and concentrated to afford methyl 4-aminocarbonyl-5-(pentan-3-ylamino)-2-(trifluoromethyl)benzoate (quantitative yield) as a yellow oil. MS (EI) for C15H19F3N2O3: 333 (MH+).

Workup

  1. temperaturewas cooled in a cold water bath
  2. customThe reaction mixture was partitioned between ethyl acetate and water
  3. extractionThe aqueous portion was extracted with ethyl acetate
  4. dry with materialThe combined organic portion was dried over sodium sulfate
  5. filtrationthen filtered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-010ab72fc4e2428dbf030a3b8e2d0f9d
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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