Sodium periodate → HCID 67189967, compound
Reaction equation
I([O-])(=O)(=O)=[O:2].[Na+].[CH:7]1([CH2:12][C@H:13]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([S:23][CH3:24])[CH:18]=2)[C:14]([OH:16])=[O:15])[CH2:11][CH2:10][CH2:9][CH2:8]1>O.CO>[CH:7]1([CH2:12][C@H:13]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([S:23]([CH3:24])=[O:2])[CH:18]=2)[C:14]([OH:16])=[O:15])[CH2:11][CH2:10][CH2:9][CH2:8]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 25 °C
Procedure
To a stirred solution of sodium periodate (1.07 g, 4.98 mmol) in water (10 mL) was added a solution of (R)-3-cyclopentyl-2-(3-methylsulfanyl-phenyl)-propionic acid (700 mg, 2.65 mmol) in methanol (15 mL) and the reaction was stirred at 25° C. for 1 h. The reaction mixture was filtered through a pad of celite and the solids were washed with methanol and chloroform. The filtrate was concentrated and azeotroped with benzene to remove any traces of water to yield (R)-3-cyclopentyl-2-(3-methylsulfinyl-phenyl)-propionic acid as a white solid which was then dissolved into methanol (20 mL). To this stirred solution was slowly added potassium permanganate (630 mg, 3.98 mmol) in water (6 mL) and the reaction stirred at 25° C. for 1 h. The reaction mixture was filtered through a pad of celite and the solids washed with methanol. Concentrate the filtrate to yield (R)-3-cyclopentyl-2-(3-methylsulfonyl-phenyl)-propionic acid (705 mg, 90%) as a white solid.
Workup
- filtrationThe reaction mixture was filtered through a pad of celite
- washthe solids were washed with methanol and chloroform
- concentrationThe filtrate was concentrated
- customazeotroped with benzene
- customto remove any traces of water
Sources & evidence
- ORD record
- ord-ba95af2f66a24828be2ad86309acc026
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07935699B2
Reaction notes
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