Hydrogen Peroxide → HCID 16125659, compound

HRID 1987471Notes

Reaction equation

HRID 1987471 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:9][CH2:10][C:11]([OH:28])([CH3:27])[C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[C:17]([C:23]([F:26])([F:25])[F:24])[CH:16]=2)=[O:13])[CH:6]=[CH:7][CH:8]=1.OO.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[OH2:44].[Cl-].[Na+].[OH2:47]>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:9]([CH2:10][C:11]([OH:28])([CH3:27])[C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[C:17]([C:23]([F:24])([F:25])[F:26])[CH:16]=2)=[O:13])(=[O:47])=[O:44])[CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 5

HCID 784Hydrogen PeroxideHCID 962WaterHCID 9845Trifluoroacetic anhydrideHCID 57417360Sodium chloride; waterHCID 68643630HCID 68643630, compound

Product 1

HCID 16125659HCID 16125659, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-(3-methoxyphenylthio)-N-(4-Cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-2-methylpropanamide (29 mg, 0.07 mmol) in dichloromethane (0.18 mL) at −78° C. was added 30% hydrogen peroxide (16 μL, 0.57 mmol) followed by the slow addition of trifluoroacetic anhydride (60 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 19 mg of desired product. Production of PLM5 was confirmed by 1-H NMR, 13-C NMR, and mass spectral analysis.

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-54607e4210704d249aef12ae840eac2a
Source dataset
uspto-grants-2009_06
Patent number
US07550505B2

Reaction notes

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