Hydrogen Peroxide → HCID 16124686, compound

HRID 1987468Notes

Reaction equation

HRID 1987468 reaction equation
[CH2:1]([C:8]1[CH:9]=[C:10]([S:14][CH2:15][C:16]([OH:33])([CH3:32])[C:17]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[C:22]([C:28]([F:31])([F:30])[F:29])[CH:21]=2)=[O:18])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OO.FC(F)(F)C(OC(=O)C(F)(F)F)=[O:39].[OH2:49]>ClCCl.[Cl-].[Na+].O>[CH2:1]([C:8]1[CH:9]=[C:10]([S:14]([CH2:15][C:16]([OH:33])([CH3:32])[C:17]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[C:22]([C:28]([F:31])([F:29])[F:30])[CH:21]=2)=[O:18])(=[O:39])=[O:49])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 9845Trifluoroacetic anhydrideHCID 68643636HCID 68643636, compound

Product 1

HCID 16124686HCID 16124686, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
-78 °C

Procedure

3-(3-benzylphenylthio)-N-(4-cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-2-methylpropanamide (15 mg, 0.033 mmol) was dissolved in dichloromethane (0.05 mL) and cooled to −78° C. 30% hydrogen peroxide (5.7 μL, 0.2 mmol) was added followed by the slow addition of trifluoroacetic anhydride (23 μL, 0.17 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 11 mg of desired product. Production of PLM3 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-fab710b73a92456e8b0e2709319f3a24
Source dataset
uspto-grants-2009_06
Patent number
US07550505B2

Reaction notes

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