Sodium periodate → HCID 69388109, compound

HRID 916820Notes

Reaction equation

HRID 916820 reaction equation
[CH:1]1([S:6][C:7]2[CH:8]=[C:9]([CH:41]=[CH:42][CH:43]=2)[CH2:10][O:11][CH2:12][CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][N:23]3[CH2:27][C@@H:26]([C:28]4[CH:39]=[CH:38][C:31]5[O:32][C:33]([CH3:37])([CH3:36])[O:34][CH2:35][C:30]=5[CH:29]=4)[O:25][C:24]3=[O:40])=[CH:17][CH:16]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.I([O-])(=O)(=O)=[O:45].[Na+]>CCO.O>[CH:1]1([S:6]([C:7]2[CH:8]=[C:9]([CH:41]=[CH:42][CH:43]=2)[CH2:10][O:11][CH2:12][CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][N:23]3[CH2:27][C@@H:26]([C:28]4[CH:39]=[CH:38][C:31]5[O:32][C:33]([CH3:37])([CH3:36])[O:34][CH2:35][C:30]=5[CH:29]=4)[O:25][C:24]3=[O:40])=[CH:17][CH:16]=2)=[O:45])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 2

HCID 23667635Sodium periodateHCID 69390257HCID 69390257, compound

Product 1

HCID 69388109HCID 69388109, compoundYield 98.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of (5R)-3-{2-[4-(2-{[3-(cyclopentylthio)benzyl]oxy}ethoxy)phenyl]ethyl}-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one (276 mg) in EtOH (15 ml) and water (5 ml) was treated with sodium periodate (391 mg) and stirred at room temperature under nitrogen for 3 h. The solution was concentrated in vacuo before pouring into water and extracting with EtOAc. The combined organic layers were washed with water, dried (MgSO4) and concentrated in vacuo to give the title compound (278 mg). LCMS RT=3.42 min.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. additionbefore pouring into water
  3. extractionextracting with EtOAc
  4. washThe combined organic layers were washed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-85bf1a66ae0c49e1a468b4ebbb5c2ca2
Source dataset
uspto-grants-2007_09
Patent number
US07271197B2

Reaction notes

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