Hydrogen Peroxide → (2S)-4-methyl-2-({(1S)-2,2,2-trifluoro-1-[4'-(methylsulfonyl)-1,1'-biphenyl-4-yl]ethyl}amino)pentan-1-ol

HRID 1009247Notes

Reaction equation

HRID 1009247 reaction equation
[CH3:1][CH:2]([CH3:27])[CH2:3][C@H:4]([NH:7][C@@H:8]([C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22](SC)=[CH:21][CH:20]=2)=[CH:15][CH:14]=1)[C:9]([F:12])([F:11])[F:10])[CH2:5][OH:6].OO.[S:30]([O-:34])([O-])(=[O:32])=S.[Na+].[Na+].[C:37](OCC)(=O)C>C1(C)C=CC=CC=1.[N+](CCCC)(CCCC)(CCCC)CCCC.[O-]S(O)(=O)=O>[CH3:1][CH:2]([CH3:27])[CH2:3][C@H:4]([NH:7][C@@H:8]([C:13]1[CH:14]=[CH:15][C:16]([C:19]2[CH:24]=[CH:23][C:22]([S:30]([CH3:37])(=[O:34])=[O:32])=[CH:21][CH:20]=2)=[CH:17][CH:18]=1)[C:9]([F:12])([F:11])[F:10])[CH2:5][OH:6]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 8857Ethyl AcetateHCID 24477Sodium ThiosulfateHCID 11502160(2S)-4-methyl-2-({(1S)-2,2,2-trifluoro-1-[4'-(methylthio)-1,1'-biphenyl-4-yl]ethyl}amino)pentan-1-ol

Product 1

HCID 11647629(2S)-4-methyl-2-({(1S)-2,2,2-trifluoro-1-[4'-(methylsulfonyl)-1,1'-biphenyl-4-yl]ethyl}amino)pentan-1-ol

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 1140TolueneSolvent

Procedure

To a 0° C. solution of the sulfide (19 g) from Step 4 in toluene (400 mL) was added Na2WO4.2H2O (0.16 g) and Bu4NHSO4 (0.81 g). Then 30% hydrogen peroxide (12.2 mL) was slowly added and the mixture was stirred at room temperature for 4.5 hours. The mixture was poured slowly on a mixture of ice, dilute aqueous sodium thiosulfate and ethyl acetate. The organic layer was separated and the aqueous further extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with brine, dried with magnesium sulfate and the solvent were removed in vacuo to yield a residue which was purified on SiO2 using ethyl acetate and hexanes (1:1) as eluant to yield the product.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous further extracted with ethyl acetate (2×100 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried with magnesium sulfate
  5. customthe solvent were removed in vacuo
  6. customto yield a residue which
  7. customwas purified on SiO2
  8. customto yield the product

Sources & evidence

ORD record
ord-42ec732db7f74b77b8ee0f17fc057e0e
Source dataset
uspto-grants-2011_07
Patent number
US07973037B2

Reaction notes

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