Water → Rabeprazole

HRID 1404619Notes

Reaction equation

HRID 1404619 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]([CH2:13][S:14][C:15]2[NH:19][C:18]3[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=3[N:16]=2)[C:8]=1[CH3:24].[OH2:25]>CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[CH3:24][C:8]1[C:9]([CH2:13][S:14]([C:15]2[NH:16][C:17]3[C:18](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:19]=2)=[O:25])=[N:10][CH:11]=[CH:12][C:7]=1[O:6][CH2:5][CH2:4][CH2:3][O:2][CH3:1]

Participants

4

Reactant 2

HCID 962WaterHCID 9949996Rabeprazole-thioether

Product 1

HCID 5029Rabeprazole

Reagents, catalysts & solvents 1

HCID 11026Titanium isopropoxideCatalyst

Procedure

In an embodiment, the process comprises contacting 2-[[[4-(3-methoxypropoxy)-3-methyl-2-pyridinyl]methyl]thio]-1H-benzimidazole (rabeprazole sulfide) with a chiral reagent in an organic solvent and water followed by addition of titanium isopropoxide. A base is added to this reaction mass followed by an oxidizing agent to obtain dexrabeprazole. The so-obtained dexrabeprazole may then be reacted with the alcoholic solution of magnesium chloride to form dexrabeprazole magnesium hydrate. Alternatively, the dexrabeprazole obtained after reaction with the oxidizing agent is converted to a salt, suitably the potassium salt, and the salt of dexrabeprazole is reacted with the alcoholic solution of magnesium chloride to form dexrabeprazole magnesium hydrate.

Workup

  1. additionA base is added to this reaction mass

Sources & evidence

ORD record
ord-8423c7475b5441d382735c69b621adef
Source dataset
uspto-grants-2014_12
Patent number
US08912337B2

Reaction notes

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