Sodium periodate → HCID 66705699, compound

HRID 1881437Notes

Reaction equation

HRID 1881437 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-f1b08071f31e4c089f86a9f5a501f5ad
Source dataset
uspto-grants-2012_11
Patent number
US08318767B2

Reaction notes

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