m-Chloroperbenzoic acid → HCID 69387116, compound

HRID 916821Notes

Reaction equation

HRID 916821 reaction equation
[CH:1]1([S:6]([C:8]2[CH:9]=[C:10]([CH:42]=[CH:43][CH:44]=2)[CH2:11][O:12][CH2:13][CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][N:24]3[CH2:28][C@@H:27]([C:29]4[CH:40]=[CH:39][C:32]5[O:33][C:34]([CH3:38])([CH3:37])[O:35][CH2:36][C:31]=5[CH:30]=4)[O:26][C:25]3=[O:41])=[CH:18][CH:17]=2)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.ClC1C=C(C=CC=1)C(OO)=[O:50]>C(Cl)Cl>[CH:1]1([S:6]([C:8]2[CH:9]=[C:10]([CH:42]=[CH:43][CH:44]=2)[CH2:11][O:12][CH2:13][CH2:14][O:15][C:16]2[CH:17]=[CH:18][C:19]([CH2:22][CH2:23][N:24]3[CH2:28][C@@H:27]([C:29]4[CH:40]=[CH:39][C:32]5[O:33][C:34]([CH3:38])([CH3:37])[O:35][CH2:36][C:31]=5[CH:30]=4)[O:26][C:25]3=[O:41])=[CH:20][CH:21]=2)(=[O:50])=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 69388109HCID 69388109, compound

Product 1

HCID 69387116HCID 69387116, compoundYield 121.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (5R)-3-{2-[4-(2-{[3-(cyclopentylsulfinyl)benzyl]oxy}ethoxy)phenyl]ethyl}-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one (56 mg) in CH2Cl2 (2 ml) was cooled in an ice bath under a nitrogen atmosphere. To this was added 3-chloroperoxybenzoic acid (30 mg) and the resulting solution was allowed to warm to room temperature and stirred for 2 h. The solution was then washed with sodium sulphite, to remove any excess peroxide, and water. The combined organic layers were then dried (MgSO4) and concentrated in vacuo to give the title compound (70 mg). LCMS RT=3.70 min.

Workup

  1. washThe solution was then washed with sodium sulphite
  2. customto remove any excess peroxide, and water
  3. dry with materialThe combined organic layers were then dried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5c6a7eec217d4914b786ea9fa97e1423
Source dataset
uspto-grants-2007_09
Patent number
US07271197B2

Reaction notes

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