m-Chloroperbenzoic acid → 2-(((4-(2-(9-Methyl-1,5,8,10-tetraoxaspiro[5.5]undec-9-yl)ethoxy)pyridin-2-yl)methyl)sulfinyl)-1h-benzimidazole sodium salt

HRID 31698Notes

Reaction equation

HRID 31698 reaction equation
[Na:1].C[C:3]1[C:4]([CH2:22][S:23]([C:25]2[NH:29][C:28]3[CH:30]=[CH:31][CH:32]=[CH:33][C:27]=3[N:26]=2)=[O:24])=[N:5][CH:6]=[CH:7][C:8]=1[O:9][CH2:10]C1(C)OCC2(OCCO2)CO1.ClC1C=CC=C(C(OO)=O)C=1.[CH3:45][C:46]1([CH2:57]CO)[O:56][CH2:55][C:49]2([O:54][CH2:53][CH2:52][CH2:51][O:50]2)[CH2:48][O:47]1>>[Na:1].[CH3:45][C:46]1([CH2:57][CH2:10][O:9][C:8]2[CH:7]=[CH:6][N:5]=[C:4]([CH2:22][S:23]([C:25]3[NH:29][C:28]4[CH:30]=[CH:31][CH:32]=[CH:33][C:27]=4[N:26]=3)=[O:24])[CH:3]=2)[O:47][CH2:48][C:49]2([O:50][CH2:51][CH2:52][CH2:53][O:54]2)[CH2:55][O:56]1

Participants

4

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 59792508HCID 59792508, compoundHCID 667765502-(((3-Methyl-4-((8-methyl-1,4,7,9-tetraoxaspiro[4.5]dec-8-yl)methoxy)pyridin-2-yl)methyl)sulfinyl)-1h-benzimidazole sodium salt

Product 1

HCID 667762652-(((4-(2-(9-Methyl-1,5,8,10-tetraoxaspiro[5.5]undec-9-yl)ethoxy)pyridin-2-yl)methyl)sulfinyl)-1h-benzimidazole sodium saltYield 11.4%

Procedure

The same procedure as in the steps (5d) to (5h) of Example 5 (a reprecipitation operation was not performed in oxidation step with 3-chloroperbenzoic acid) was repeated using 2-(9-methyl-1,5,8,10-tetraoxaspiro[5.5]undec-9-yl)ethanol obtained in the step (76d) above to obtain the title compound (228 mg, total 11.4% yield) as a white solid.

Workup

  1. customobtained in the step (76d) above

Sources & evidence

ORD record
ord-fa15aa8ebb394b6f8b03fb1b2798906b
Source dataset
uspto-grants-2008_09
Patent number
US07425634B2

Reaction notes

Loading…