Hydrogen Peroxide → HCID 68643669, compound

HRID 1987472Notes

Reaction equation

HRID 1987472 reaction equation
[C:1]1([C:7]2([S:13][CH2:14][C:15]([OH:32])([CH3:31])[C:16]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[C:21]([C:27]([F:30])([F:29])[F:28])[CH:20]=3)=[O:17])[CH:12]=[CH:11][CH:10]=[CH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.OO.FC(F)(F)C(OC(=O)C(F)(F)F)=[O:38].[OH2:48]>ClCCl.[Cl-].[Na+].O>[C:1]1([C:7]2([S:13]([CH2:14][C:15]([OH:32])([CH3:31])[C:16]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[C:21]([C:27]([F:28])([F:29])[F:30])[CH:20]=3)=[O:17])(=[O:38])=[O:48])[CH:8]=[CH:9][CH:10]=[CH:11][CH2:12]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 9845Trifluoroacetic anhydrideHCID 68643591HCID 68643591, compound

Product 1

HCID 68643669HCID 68643669, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 3-(1-phenylphenylthio)-N-(4-Cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-2-methylpropanamide (85 mg, 0.21 mmol) in dichloromethane (0.3 mL) at −78° C. was added 30% hydrogen peroxide (0.036 mL, 1.26 mmol) followed by the slow addition of trifluoroacetic anhydride (0.151 mL, 1.07 mmol). The reaction was stirred at room temperature for 16 h. The reaction was diluted with dichloromethane. Cold water and brine were added, and the reaction was stirred for 20 minutes. The organic layer was separated, dried over magnesium sulfate, filtered and evaporated. Purification by column chromatography (hexane:EtOAc 50:50) yielded 41 mg of desired product.

Workup

  1. stirringthe reaction was stirred for 20 minutes
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by column chromatography (hexane:EtOAc 50:50)

Sources & evidence

ORD record
ord-afe372b4583446fdbdef10588a9dfc84
Source dataset
uspto-grants-2009_06
Patent number
US07550505B2

Reaction notes

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