Sodium periodate → HCID 66705699, compound

HRID 425357Notes

Reaction equation

HRID 425357 reaction equation
I([O-])(=O)(=O)=[O:2].[Na+].[CH3:7][C:8]([CH3:41])([CH2:39][CH3:40])[CH2:9][C:10]1[N:11]=[C:12]([C:21]([OH:38])([CH3:37])[CH2:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[S:35][CH3:36])=[CH:25][CH:24]=2)[N:13]([S:15]([N:18]([CH3:20])[CH3:19])(=[O:17])=[O:16])[CH:14]=1>C(O)C.O>[CH3:7][C:8]([CH3:41])([CH2:39][CH3:40])[CH2:9][C:10]1[N:11]=[C:12]([C:21]([OH:38])([CH3:37])[CH2:22][C:23]2[CH:24]=[CH:25][C:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[S:35]([CH3:36])=[O:2])=[CH:27][CH:28]=2)[N:13]([S:15]([N:18]([CH3:19])[CH3:20])(=[O:16])=[O:17])[CH:14]=1

Participants

4

Reactant 2

HCID 23667635Sodium periodateHCID 66705828HCID 66705828, compound

Product 1

HCID 66705699HCID 66705699, compound

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

Sodium periodate (40 mg, 0.19 mmol) was added to an ambient temperature solution of 4-(2,2-dimethylbutyl)-2-{1-hydroxy-1-methyl-2-[2′-(methylthio)biphenyl-4-yl]ethyl}-N,N-dimethyl-1H-imidazole-1-sulfonamide (65 mg, 0.13 mmol) in ethanol/water (1:1) (5 mL). After stirring at ambient temperature until no further reaction (LCMS), the reaction mixture was quenched with saturated aqueous sodium thiosulfate and extracted with methylene chloride. Combined extracts were dried (magnesium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-30% acetone/methylene chloride afforded 4-(2,2-dimethylbutyl)-2-{1-hydroxy-1-methyl-2-[2′-(methylsulfinyl)biphenyl-4-yl]ethyl}-N,N-dimethyl-1H-imidazole-1-sulfonamide.

Workup

  1. customthe reaction mixture was quenched with saturated aqueous sodium thiosulfate
  2. extractionextracted with methylene chloride
  3. dry with materialCombined extracts were dried (magnesium sulfate)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-27e0966d1de14b8c99d54dc3f72b3009
Source dataset
uspto-grants-2012_01
Patent number
US08106070B2

Reaction notes

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