Sodium Thiosulfate → Ethyl 3-cyclopropyl-3-(3-(((2'-fluoro-5'-methoxy-2-neopentyl-[1,1'-biphenyl]-4-yl)sulfinyl)methyl)phenyl)propanoate

HRID 1049447Notes

Reaction equation

HRID 1049447 reaction equation
[CH:1]1([CH:4]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][S:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]4[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:26]=4[F:33])=[C:21]([CH2:34][C:35]([CH3:38])([CH3:37])[CH3:36])[CH:20]=3)[CH:12]=2)[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:3][CH2:2]1.I([O-])(=O)(=O)=[O:40].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>CO.O>[CH:1]1([CH:4]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][S:18]([C:19]3[CH:24]=[CH:23][C:22]([C:25]4[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:26]=4[F:33])=[C:21]([CH2:34][C:35]([CH3:37])([CH3:36])[CH3:38])[CH:20]=3)=[O:40])[CH:12]=2)[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 24477Sodium ThiosulfateHCID 23667635Sodium periodateHCID 117759924Ethyl 3-cyclopropyl-3-(3-(((2'-fluoro-5'-methoxy-2-neopentyl-[1,1'-biphenyl]-4-yl)thio)methyl)phenyl)propanoate

Product 1

HCID 117759651Ethyl 3-cyclopropyl-3-(3-(((2'-fluoro-5'-methoxy-2-neopentyl-[1,1'-biphenyl]-4-yl)sulfinyl)methyl)phenyl)propanoateYield 87.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of ethyl 3-cyclopropyl-3-(3-(((2′-fluoro-5′-methoxy-2-neopentyl-[1,1′-biphenyl]-4-yl)thio)methyl)phenyl)propanoate (158 mg) in methanol (0.95 mL) was added a solution of sodium periodate (66 mg) in water (50 μL), and the mixture was stirred at room temperature for 7 hr. To the reaction mixture was added saturated aqueous sodium thiosulfate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (143 mg) as a colorless oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-569361f609394661930bf67527251e1e
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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