m-Chloroperbenzoic acid → 2-(((3-Methyl-4-(2-(2-methyl-1,3-dioxolan-2-yl)ethoxy)pyridin-2-yl)methyl)sulfinyl)-1h-benzimidazole sodium salt

HRID 31693Notes

Reaction equation

HRID 31693 reaction equation
[Na:1].C(C1(C[CH2:15][O:16][C:17]2[CH:22]=[CH:21][N:20]=[C:19]([CH2:23][S:24]([C:26]3[NH:30][C:29]4[CH:31]=[CH:32][CH:33]=[CH:34][C:28]=4[N:27]=3)=[O:25])[C:18]=2[CH3:35])OCC2(OCCO2)CO1)C.ClC1C=CC=C(C(OO)=O)C=1.[CH3:47][C:48]1([CH2:53]CO)[O:52][CH2:51][CH2:50][O:49]1>>[Na:1].[CH3:35][C:18]1[C:19]([CH2:23][S:24]([C:26]2[NH:27][C:28]3[CH:34]=[CH:33][CH:32]=[CH:31][C:29]=3[N:30]=2)=[O:25])=[N:20][CH:21]=[CH:22][C:17]=1[O:16][CH2:15][CH2:47][C:48]1([CH3:53])[O:52][CH2:51][CH2:50][O:49]1

Participants

4

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 5383821,3-Dioxolane-2-ethanol, 2-methyl-HCID 667761962-(((4-(2-(8-Ethyl-1,4,7,9-tetraoxaspiro[4.5]dec-8-yl)ethoxy)-3-methylpyridin-2-yl)methyl)sulfinyl)-1h-benzimidazole sodium salt

Product 1

HCID 667765012-(((3-Methyl-4-(2-(2-methyl-1,3-dioxolan-2-yl)ethoxy)pyridin-2-yl)methyl)sulfinyl)-1h-benzimidazole sodium saltYield 14.4%

Procedure

The same procedure as in the steps (4f) to (4j) of Example 4 (a reprecipitation operation was not performed in oxidation step with 3-chloroperbenzoic acid) was repeated using 2-(2-methyl-1,3-dioxolan-2-yl)ethanol obtained in the step (69b) to obtain the title compound (410 mg, total 14.4% yield) as a light yellow solid.

Workup

  1. customobtained in the step (69b)

Sources & evidence

ORD record
ord-fdddb299e0ed48af9b5603c67183e2b3
Source dataset
uspto-grants-2008_09
Patent number
US07425634B2

Reaction notes

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