2,2-Diethyl-1,3-dioxolane-4-methanol → 2-(((4-((2,2-Diethyl-1,3-dioxolan-4-yl)methoxy)-3-methylpyridin-2-yl)methyl)sulfinyl)-1h-benzimidazole sodium salt

HRID 31686Notes

Reaction equation

HRID 31686 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.[CH2:47]([C:49]1([CH2:56][CH3:57])[O:53][CH:52]([CH2:54][OH:55])[CH2:51][O:50]1)[CH3:48]>>[Na:1].[CH2:56]([C:49]1([CH2:47][CH3:48])[O:53][CH:52]([CH2:54][O:55][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])[CH2:51][O:50]1)[CH3:57]

Participants

4

Reactant 3

HCID 219022,2-Diethyl-1,3-dioxolane-4-methanolHCID 70297m-Chloroperbenzoic acidHCID 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 667756402-(((4-((2,2-Diethyl-1,3-dioxolan-4-yl)methoxy)-3-methylpyridin-2-yl)methyl)sulfinyl)-1h-benzimidazole sodium saltYield 14.3%

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-diethyl-1,3-dioxolan-4-yl)methanol obtained in the step (65b) above to obtain the title compound (418 mg, total 14.3% yield) as a light yellow solid.

Workup

  1. customobtained in the step (65b) above

Sources & evidence

ORD record
ord-c4f9e9966dc740ad87c6126e9a627e98
Source dataset
uspto-grants-2008_09
Patent number
US07425634B2

Reaction notes

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