Hydrogen Peroxide → HCID 118492062, compound

HRID 711337Notes

Reaction equation

HRID 711337 reaction equation
[CH3:1][N:2]([C@@H:9]([C:12]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[C:14](B2OC(C)(C)C(C)(C)O2)[CH:13]=1)[CH:10]=[CH2:11])[S@:3]([C:5]([CH3:8])([CH3:7])[CH3:6])=[O:4].[OH-:31].[Na+].OO>C1COCC1>[OH:31][C:14]1[CH:13]=[C:12]([C@H:9]([N:2]([CH3:1])[S@:3]([C:5]([CH3:8])([CH3:7])[CH3:6])=[O:4])[CH:10]=[CH2:11])[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 123424721HCID 123424721, compound

Product 1

HCID 118492062HCID 118492062, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-N,2-dimethyl-N-((R)-1-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5-(trifluoromethyl)phenyl)allyl)propane-2-sulfinamide (800 mg, 1.8 mmol) and NaOH (144 mg, 3.6 mmol) in THF (10 mL), was added H2O2 (122 mg, 3.6 mmol) at 0° C. The reaction mixture was allowed to warm to room temperature and stirred for 2 h. After quenched with water, the resulting mixture was extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous Na2SO4. and then concentrated to give the title compound (500 mg, yield: 83%); m/z (ES+): 336 [M+H]+.

Workup

  1. customAfter quenched with water
  2. extractionthe resulting mixture was extracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationand then concentrated

Sources & evidence

ORD record
ord-2802a349b59e437780b7d598673b4222
Source dataset
uspto-grants-2015_11
Patent number
US09181259B2

Reaction notes

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