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

HRID 2118323Notes

Reaction equation

HRID 2118323 reaction equation
I([O-])(=O)(=O)=[O:2].[Na+].[CH:7]1([S:12][C:13]2[CH:14]=[C:15]([CH2:19][CH2:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][N:30]3[CH2:34][C@@H:33]([C:35]4[CH:46]=[CH:45][C:38]5[O:39][C:40]([CH3:44])([CH3:43])[O:41][CH2:42][C:37]=5[CH:36]=4)[O:32][C:31]3=[O:47])[CH:16]=[CH:17][CH:18]=2)[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]([CH2:19][CH2:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][N:30]3[CH2:34][C@@H:33]([C:35]4[CH:46]=[CH:45][C:38]5[O:39][C:40]([CH3:43])([CH3:44])[O:41][CH2:42][C:37]=5[CH:36]=4)[O:32][C:31]3=[O:47])[CH:16]=[CH:17][CH:18]=2)=[O:2])[CH2:8][CH2:9][CH2:10][CH2:11]1

Participants

5

Reactant 2

HCID 23667635Sodium periodateHCID 69119396(5R)-3-(6-{4-[3-(Cyclopentylthio)phenyl]butoxy}hexyl)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one

Product 1

HCID 69119380(5R)-3-(6-{4-[3-(Cyclopentylsulfinyl)phenyl]butoxy}hexyl)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-oneYield 66.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Sodium periodate (1.5 g) was added to a stirred solution of (5R)-3-(6-{4-[3-(cyclopentylthio)phenyl]butoxy}hexyl)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one (1.0 g) in ethanol (20 ml) and water (10 ml) at room temperature. After 2 h the solution was concentrated in-vacuo (ca 50% vol), diluted with water and extracted into dichloromethane. The extracts were dried (Na2SO4) and evaporated to dryness. The residual oil was purified on a biotage cartridge (40 g) using ethyl acetate as the eluent. The appropriate fractions were evaporated to give the title compound (0.68 g). LCMS RT=3.66 min

Workup

  1. concentrationAfter 2 h the solution was concentrated in-vacuo (ca 50% vol)
  2. additiondiluted with water
  3. extractionextracted into dichloromethane
  4. dry with materialThe extracts were dried (Na2SO4)
  5. customevaporated to dryness
  6. customThe residual oil was purified on a biotage cartridge (40 g)
  7. customThe appropriate fractions were evaporated

Sources & evidence

ORD record
ord-2b1081ae73ea4cde93439419629f56c3
Source dataset
uspto-grants-2008_10
Patent number
US07442839B2

Reaction notes

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