Hydrogen Peroxide → HCID 16125657, compound

HRID 1987470Notes

Reaction equation

HRID 1987470 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[S:13][CH2:14][C:15]([OH:32])([CH3:31])[C:16]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[C:21]([C:27]([F:30])([F:29])[F:28])[CH:20]=2)=[O:17])[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[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[S:13]([CH2:14][C:15]([OH:32])([CH3:31])[C:16]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[C:21]([C:27]([F:28])([F:29])[F:30])[CH:20]=2)=[O:17])(=[O:38])=[O:48])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 9845Trifluoroacetic anhydrideHCID 68643634HCID 68643634, compound

Product 1

HCID 16125657HCID 16125657, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 3-(2-phenylphenylthio)-N-(4-Cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-2-methylpropanamide (41 mg, 0.093 mmol) in dichloromethane (0.13 mL) at −78° C. was added 30% hydrogen peroxide (15.5 μL, 0.54 mmol) followed by the slow addition of trifluoroacetic anhydride (63 μL, 0.45 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 23 mg of desired product. Production of PLM4 was confirmed by 1-H NMR and 13-C NMR.

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-95b7eef9a3ac4e20b99c44c2e9ae6dd0
Source dataset
uspto-grants-2009_06
Patent number
US07550505B2

Reaction notes

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