Sodium periodate → HCID 86638503, compound

HRID 216390Notes

Reaction equation

HRID 216390 reaction equation
I([O-])(=O)(=O)=O.[Na+].[F:7][CH:8]([F:57])[C:9]([C:44]1[CH:49]=[CH:48][C:47]([C:50]2[CH:55]=[CH:54][C:53]([F:56])=[CH:52][N:51]=2)=[CH:46][CH:45]=1)([OH:43])[CH2:10][C:11]1[N:12]([C:24]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:13]=[C:14]([CH2:16][C:17]([CH3:23])([CH3:22])[CH:18]([OH:21])CO)[N:15]=1>O1CCCC1.O>[F:57][CH:8]([F:7])[C:9]([C:44]1[CH:45]=[CH:46][C:47]([C:50]2[CH:55]=[CH:54][C:53]([F:56])=[CH:52][N:51]=2)=[CH:48][CH:49]=1)([OH:43])[CH2:10][C:11]1[N:12]([C:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:13]=[C:14]([CH2:16][C:17]([CH3:23])([CH3:22])[CH:18]=[O:21])[N:15]=1

Participants

4

Reactant 2

HCID 23667635Sodium periodateHCID 68668307HCID 68668307, compound

Product 1

HCID 86638503HCID 86638503, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Sodium periodate was added to a solution of 4-(2-{3,3-difluoro-2-[4-(5-fluoropyridin-2-yl)phenyl]-2-hydroxypropyl}-1-trityl-1H-imidazol-4-yl)-3,3-dimethylbutane-1,2-diol (300 mg, 0.43 mmol) in tetrahydrofuran/water (2:1) (10 mL) at 0° C. After stirring at ambient temperature until complete (by LCMS), the reaction mixture was quenched with saturated aqueous sodium bicarbonate and extracted with methylene chloride. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-40% ethyl acetate/hexane afforded 3-(2-{3,3-difluoro-2-[4-(5-fluoropyridin-2-yl)phenyl]-2-hydroxypropyl}-1-trityl-1H-imidazol-4-yl)-2,2-dimethylpropanal.

Workup

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

Sources & evidence

ORD record
ord-8d1e0a1ec2f84f34ade29a2e0b3b1ee1
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Reaction notes

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