Water → Rabeprazole

HRID 1404620Notes

Reaction equation

HRID 1404620 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 another aspect of the present invention, there is provided a process for the preparation of crystalline dexrabeprazole magnesium hydrate. The process comprises contacting 2-[[[4-(3-methoxypropoxy)-3-methyl-2-pyridinyl]methyl]thio]-1H-benzimidazole with a chiral reagent in an organic solvent and water followed by addition of titanium isopropoxide. The base is added to this reaction mass followed by an oxidizing agent to obtain dexrabeprazole. The so obtained dexrabeprazole is then treated with suitable inorganic salt of magnesium to obtain corresponding dexrabeprazole magnesium salt. This magnesium salt is optionally purified from a suitable organic solvent. In an embodiment, the dexrabeprazole magnesium hydrate is in crystalline form, and the preparation of the crystalline form comprises reacting the dexrabeprazole with an alcoholic (preferably methanolic) solution of magnesium chloride.

Workup

  1. customIn another aspect of the present invention, there is provided a process
  2. additionThe base is added to this reaction mass

Sources & evidence

ORD record
ord-87d6e12824104057a9ca34b3bfe13210
Source dataset
uspto-grants-2014_12
Patent number
US08912337B2

Reaction notes

Loading…