Sodium Thiosulfate → Trifluoroacetic acid

HRID 70711Notes

Reaction equation

HRID 70711 reaction equation
ClC1C=CC=[C:4]([C:8](OO)=O)[CH:3]=1.[CH:12]1([O:17][CH:18]([C:30]2[CH:35]=[CH:34][C:33](SC3CC3)=[CH:32][CH:31]=2)[C:19]2[NH:24][C:23](=[O:25])[C:22]([C:26]([F:29])([F:28])[F:27])=[CH:21][CH:20]=2)[CH2:16][CH2:15][CH2:14][CH2:13]1.[S:40]([O-:44])([O-])(=[O:42])=S.[Na+].[Na+].[C:47](=[O:50])(O)[O-:48].[Na+]>C(Cl)(Cl)Cl>[F:27][C:26]([F:29])([F:28])[C:47]([OH:48])=[O:50].[CH:12]1([O:17][CH:18]([C:30]2[CH:31]=[CH:32][C:33]([S:40]([CH:8]3[CH2:4][CH2:3]3)(=[O:44])=[O:42])=[CH:34][CH:35]=2)[C:19]2[NH:24][C:23](=[O:25])[C:22]([C:26]([F:29])([F:27])[F:28])=[CH:21][CH:20]=2)[CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

7

Reactant 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 58452349HCID 58452349, compound

Product 2

HCID 6422Trifluoroacetic acidYield 0.1%HCID 58452908HCID 58452908, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3-Chloroperbenzoic acid (31 mg) was added to a solution of 6-{(cyclopentyloxy)[4-(cyclopropylsulfanyl)phenyl]methyl}-3-(trifluoromethyl)pyridin-2(1H)-one (25 mg) in chloroform (1 mL), and the mixture was stirred at room temperature overnight. A sodium thiosulfate solution and aqueous sodium bicarbonate were added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, after which the solvent was evaporated under reduced pressure. The residue was purified by preparative HPLC (Waters Sunfire 19×150 mm 5 μm, rate: 20 mL/min, eluent: A=acetonitrile, B=0.1% trifluoroacetic acid solution, gradient: 10 to 90%) to give the title compound as a colorless amorphous (7 mg, 26%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customafter which the solvent was evaporated under reduced pressure
  4. customThe residue was purified by preparative HPLC (Waters Sunfire 19×150 mm 5 μm, rate

Sources & evidence

ORD record
ord-01c13c1fe8664388bf3b8405f5196636
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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