Hydrogen Peroxide → HCID 24768099, compound

HRID 1987473Notes

Reaction equation

HRID 1987473 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([S:12][CH2:13][C:14]([OH:31])([CH3:30])[C:15]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[C:20]([C:26]([F:29])([F:28])[F:27])[CH:19]=2)=[O:16])=[CH:4][CH:3]=1.OO.FC(F)(F)C(OC(=O)C(F)(F)F)=[O:37].[OH2:47]>ClCCl.[Cl-].[Na+].O>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([S:12]([CH2:13][C:14]([OH:31])([CH3:30])[C:15]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[C:20]([C:26]([F:27])([F:28])[F:29])[CH:19]=2)=[O:16])(=[O:37])=[O:47])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 9845Trifluoroacetic anhydrideHCID 68643664HCID 68643664, compound

Product 1

HCID 24768099HCID 24768099, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 3-(1-bromonaphthalen-4-ylthio)-N-(4-Cyano-3-(trifluoromethyl)phenyl)-2-hydroxy-2-methylpropanamide (13 mg, 0.025 mmol) in dichloromethane (0.06 mL) at −78° C. was added 30% hydrogen peroxide (4.4 μL, 0.155 mmol) followed by the slow addition of trifluoroacetic anhydride (18 μL, 0.13 mmol). The reaction was stirred at room temperature for 16 h before 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 9 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-e5c2d4b342104aa7a9dfb0a67c58b1cb
Source dataset
uspto-grants-2009_06
Patent number
US07550505B2

Reaction notes

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