Hydrogen Peroxide → HCID 57937844, compound

HRID 1435060Notes

Reaction equation

HRID 1435060 reaction equation
[C:1]([O:5][C:6](=[O:31])[N:7]([CH2:13][C:14]1[C:19]([F:20])=[CH:18][C:17]([C:21]2[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][C:22]=2[CH3:29])=[CH:16][C:15]=1[F:30])[CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-:33].[K+].[K+].OO>CS(C)=O.O>[C:1]([O:5][C:6](=[O:31])[N:7]([CH2:13][C:14]1[C:19]([F:20])=[CH:18][C:17]([C:21]2[CH:26]=[CH:25][C:24]([C:27](=[O:33])[NH2:28])=[CH:23][C:22]=2[CH3:29])=[CH:16][C:15]=1[F:30])[CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 68902017HCID 68902017, compound

Product 1

HCID 57937844HCID 57937844, compoundYield 89.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

(4′-Cyano-3,5-difluoro-2′-methyl-biphenyl-4-ylmethyl)-(3-methyl-butyl)-carbamic acid tert-butyl ester (I-1d: 30 g) was dissolved in 150 mL dimethyl sulfoxide and combined with potassium carbonate (20 g) and 20 mL of a 30% hydrogen peroxide solution in water. After stirring at room temperature for 12 hours, the reaction mixture was quenched with water and extracted using ethyl acetate (250 mL). The organic layer was washed with water (2 times), brine, dried over magnesium sulfate, filtered and concentrated. The residue was purified by chromatography on silica eluting with 50% ethyl acetate in heptane to provide 28 g of the title compound (I-1e).

Workup

  1. customthe reaction mixture was quenched with water
  2. extractionextracted
  3. washThe organic layer was washed with water (2 times), brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica eluting with 50% ethyl acetate in heptane

Sources & evidence

ORD record
ord-6aee94a6d46542afbf94b1021d547a3d
Source dataset
uspto-grants-2009_11
Patent number
US07615651B2

Reaction notes

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