m-Chloroperbenzoic acid → (5R)-3-(6-{4-[3-(Cyclopentylsulfonyl)phenyl]butoxy}hexyl)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one

HRID 2118326Notes

Reaction equation

HRID 2118326 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH:12]1([S:17]([C:19]2[CH:20]=[C:21]([CH2:25][CH2:26][CH2:27][CH2:28][O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][N:36]3[CH2:40][C@@H:39]([C:41]4[CH:52]=[CH:51][C:44]5[O:45][C:46]([CH3:50])([CH3:49])[O:47][CH2:48][C:43]=5[CH:42]=4)[O:38][C:37]3=[O:53])[CH:22]=[CH:23][CH:24]=2)=[O:18])[CH2:16][CH2:15][CH2:14][CH2:13]1>C(Cl)Cl>[CH:12]1([S:17]([C:19]2[CH:20]=[C:21]([CH2:25][CH2:26][CH2:27][CH2:28][O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][N:36]3[CH2:40][C@@H:39]([C:41]4[CH:52]=[CH:51][C:44]5[O:45][C:46]([CH3:49])([CH3:50])[O:47][CH2:48][C:43]=5[CH:42]=4)[O:38][C:37]3=[O:53])[CH:22]=[CH:23][CH:24]=2)(=[O:6])=[O:18])[CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 69119380(5R)-3-(6-{4-[3-(Cyclopentylsulfinyl)phenyl]butoxy}hexyl)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one

Product 1

HCID 69119376(5R)-3-(6-{4-[3-(Cyclopentylsulfonyl)phenyl]butoxy}hexyl)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-oneYield 85.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-Chloroperoxybenzoic acid (0.088 g) was added to a stirred, cooled (ice-bath) solution of (5R)-3-(6-{4-[3-(cyclopentylsulfinyl)phenyl]butoxy}hexyl)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one (0.097 g) in DCM (10 ml). The solution was stirred for 0.5 h at room temperature. The solution was diluted with DCM and washed with 2N NaOH solution, water, dried (Na2SO4) and evaporated to give the title compound (0.085 g)

Workup

  1. washwashed with 2N NaOH solution, water
  2. dry with materialdried (Na2SO4)
  3. customevaporated

Sources & evidence

ORD record
ord-d065a792ae9e4ddf89d343261b144179
Source dataset
uspto-grants-2008_10
Patent number
US07442839B2

Reaction notes

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