3,3-Dimethyl-1,5-dioxaspiro[5.5]undecan-9-ol → 2-(((4-((3,3-Dimethyl-1,5-dioxaspiro[5.5]undec-9-yl)oxy)-3-methylpyridin-2-yl)methyl)sulfinyl)-1h-benzimidazole sodium salt

HRID 31706

Reaction equation

HRID 31706 reaction equation
[Na:1].CC1(C)O[C@H](C[O:9][C:10]2[CH:15]=[CH:14][N:13]=[C:12]([CH2:16][S:17]([C:19]3[NH:23][C:22]4[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=4[N:20]=3)=[O:18])[C:11]=2[CH3:28])CO1.[CH3:30][C:31]1([CH3:43])[CH2:36][O:35][C:34]2([CH2:41][CH2:40][CH:39](O)[CH2:38][CH2:37]2)[O:33][CH2:32]1>>[Na:1].[CH3:30][C:31]1([CH3:43])[CH2:32][O:33][C:34]2([CH2:37][CH2:38][CH:39]([O:9][C:10]3[CH:15]=[CH:14][N:13]=[C:12]([CH2:16][S:17]([C:19]4[NH:23][C:22]5[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=5[N:20]=4)=[O:18])[C:11]=3[CH3:28])[CH2:40][CH2:41]2)[O:35][CH2:36]1

Participants

3

Reactant 2

HCID 124700963,3-Dimethyl-1,5-dioxaspiro[5.5]undecan-9-olHCID 667765522-(((4-(((4r)-2,2-Dimethyl-1,3-dioxolan-4-yl)methoxy)-3-methylpyridin-2-yl)methyl)sulfinyl)-1h-benzimidazole sodium salt

Product 1

HCID 667764562-(((4-((3,3-Dimethyl-1,5-dioxaspiro[5.5]undec-9-yl)oxy)-3-methylpyridin-2-yl)methyl)sulfinyl)-1h-benzimidazole sodium salt

Procedure

The same procedure as in the steps (14a) to (14e) of Example 14 was repeated using the 3,3-dimethyl-1,5-dioxaspiro[5.5]undecan-9-ol obtained in the step (81a) above to obtain the title compound (275 mg, the total yield of 5 steps: 3.3%) as a white solid. Note that in the same process as in the step (14b), after acetic anhydride was added, 10 equivalents of triethylamine relative to pyridine1-oxide derivative was added to perform the reaction. In the same process as in the step (14c), tetrahydrofuran was used as a solvent instead of ethanol.

Workup

  1. customobtained in the step (81a) above

Sources & evidence

ORD record
ord-515b25f2ec0c40cfa20553cc95a80cf8
Source dataset
uspto-grants-2008_09
Patent number
US07425634B2

Linked notes

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