m-Chloroperbenzoic acid → 2-(((4-(1,3-Dioxolan-2-ylmethoxy)-3-methylpyridin-2-yl)methyl)sulfinyl)-1h-benzimidazole sodium salt

HRID 31688Notes

Reaction equation

HRID 31688 reaction equation
[Na:1].C(C1(CCO[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.[O:47]1[CH2:51][CH2:50][O:49][CH:48]1[CH2:52][OH:53]>>[Na:1].[O:47]1[CH2:51][CH2:50][O:49][CH:48]1[CH2:52][O:53][C:17]1[CH:22]=[CH:21][N:20]=[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])[C:18]=1[CH3:35]

Participants

4

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 2948641,3-Dioxolane-2-methanolHCID 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 667761432-(((4-(1,3-Dioxolan-2-ylmethoxy)-3-methylpyridin-2-yl)methyl)sulfinyl)-1h-benzimidazole sodium saltYield 17.2%

Procedure

The same procedure as in the steps (4f) to (4j) described in Example (a reprecipitation operation was not performed in oxidation step with 3-chloroperbenzoic acid) was repeated using 1,3-dioxolan-2-ylmethanol obtained in the step (66b) above to obtain the title compound (411 mg, total 17.2% yield) as a white solid.

Workup

  1. customobtained in the step (66b) above

Sources & evidence

ORD record
ord-6cce90727242492db6a803abb073bfd3
Source dataset
uspto-grants-2008_09
Patent number
US07425634B2

Reaction notes

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