Sodium periodate → (5R)-3-[6-(2-{[3-(Cyclopentylsulfinyl)benzyl]oxy}ethoxy)hexyl]-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one

HRID 2116994Notes

Reaction equation

HRID 2116994 reaction equation
I([O-])(=O)(=O)=[O:2].[Na+].[CH:7]1([S:12][C:13]2[CH:14]=[C:15]([CH:45]=[CH:46][CH:47]=2)[CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][N:27]2[CH2:31][C@@H:30]([C:32]3[CH:43]=[CH:42][C:35]4[O:36][C:37]([CH3:41])([CH3:40])[O:38][CH2:39][C:34]=4[CH:33]=3)[O:29][C:28]2=[O:44])[CH2:11][CH2:10][CH2:9][CH2:8]1>C(O)C.O>[CH:7]1([S:12]([C:13]2[CH:14]=[C:15]([CH:45]=[CH:46][CH:47]=2)[CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][N:27]2[CH2:31][C@@H:30]([C:32]3[CH:43]=[CH:42][C:35]4[O:36][C:37]([CH3:41])([CH3:40])[O:38][CH2:39][C:34]=4[CH:33]=3)[O:29][C:28]2=[O:44])=[O:2])[CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

5

Reactant 2

HCID 23667635Sodium periodateHCID 66845210(5R)-3-[6-(2-{[3-(cyclopentylthio)benzyl]oxy}ethoxy)hexyl]-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one

Product 1

HCID 66845815(5R)-3-[6-(2-{[3-(Cyclopentylsulfinyl)benzyl]oxy}ethoxy)hexyl]-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-oneYield 85.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Sodium periodate (333 mg) was added to a solution of (5R)-3-[6-(2-{[3-(cyclopentylthio)benzyl]oxy}ethoxy)hexyl]-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one (230 mg) in ethanol (12 ml) and water (4 ml). The mixture was stirred at room temperature under nitrogen for 3 h. and the ethanol evaporated in vacuo. The aqueous phase was diluted with water and extracted with ethyl acetate. The combined ethyl acetate extracts were dried (MgSO4) filtered, and evaporated in vacuo. The residue was purified on a 10 g silica SPE cartridge, eluting with a stepped gradient of 10% to 100% ethyl acetate-cyclohexane, to give the title compound (201 mg). LCMS RT=3.54 min.

Workup

  1. customthe ethanol evaporated in vacuo
  2. additionThe aqueous phase was diluted with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined ethyl acetate extracts were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was purified on a 10 g silica SPE cartridge
  8. washeluting with a stepped gradient of 10% to 100% ethyl acetate-cyclohexane

Sources & evidence

ORD record
ord-7786f44b4da246ab931f2e4b22e99479
Source dataset
uspto-grants-2008_10
Patent number
US07439393B2

Reaction notes

Loading…