Hydrogen Peroxide → HCID 58696376, compound

HRID 1178345Notes

Reaction equation

HRID 1178345 reaction equation
[C:1]1([O:7][C:8](=[O:33])[N:9]([C@:11]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([Cl:32])[CH:26]=2)([CH2:22][CH:23]=[CH2:24])[CH2:12][N:13]([CH3:21])[C:14](=[O:20])[CH2:15][C:16]([F:19])([F:18])[F:17])[CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH2:34].[OH-].[Na+].OO>O1CCCC1>[C:1]1([O:7][C:8](=[O:33])[N:9]([C@:11]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([Cl:32])[CH:26]=2)([CH2:22][CH2:23][CH2:24][OH:34])[CH2:12][N:13]([CH3:21])[C:14](=[O:20])[CH2:15][C:16]([F:19])([F:18])[F:17])[CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 14798Sodium HydroxideHCID 58696339HCID 58696339, compound

Product 1

HCID 58696376HCID 58696376, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under argon, phenyl[1-(3,3,3-trifluoro-N-methylpropanamido)-2-(S)-(3,4-dichlorophenyl)-4-penten-2-yl]methylcarbamate (410 mg) was dissolved in anhydrous tetrahydrofuran (4 mL). Under cooling with ice, a 1.06M solution (0.80 mL) of borane tetrahydrofuran complex in tetrahydrofuran was added thereto, and the mixture was stirred for 1 hour. Water (0.3 mL), 3N aqueous sodium hydroxide (0.9 mL), and 30% aqueous hydrogen peroxide (0.9 mL) were added to the reaction mixture, and the resultant mixture was stirred for 1 hour at room temperature. The reaction mixture was extracted with ethyl acetate, sequentially washed with water and saturated brine, and dried over sodium sulfate anhydrate. The solvent was concentrated under reduced pressure, and the residue was purified through silica gel column chromatography (n-hexane:ethyl acetate=1:2), to thereby give the title compound (311 mg, 70.0%).

Workup

  1. temperatureUnder cooling with ice
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. washsequentially washed with water and saturated brine
  4. dry with materialdried over sodium sulfate anhydrate
  5. concentrationThe solvent was concentrated under reduced pressure
  6. customthe residue was purified through silica gel column chromatography (n-hexane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-e710eef61b4e4dca9e2be223a31bf47d
Source dataset
uspto-grants-2007_10
Patent number
US07276511B2

Reaction notes

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