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Rabeprazole is a proton pump inhibitor (PPI) drug used to treat conditions such as gastroesophageal reflux disease (GERD), peptic ulcer disease, and Zollinger-Ellison syndrome.
The synthesis of rabeprazole involves several steps, which can be divided into synthetic routes.
In this article, we will discuss two of the most commonly used synthetic routes for rabeprazole: the literature method and the simplified method.
Literature Method
The literature method is a well-established synthetic route for rabeprazole that involves the synthesis of the intermediate 2-[(3,4-dichlorophenyl)methyl]-N-(2,2,2-trifluoroethyl)acetamide, also known as WO 87/01283 A2 intermediate.
This intermediate is then transformed into rabeprazole through a series of chemical reactions.
The synthesis of the WO 87/01283 A2 intermediate begins with the reaction of 2,3-dichlorophenyl acetate with potassium carbonate in the presence of a solvent such as DMF or DMSO.
The resulting product is then treated with trifluoroethylamine in the presence of a solvent such as N,N-dimethylacetamide or N,N-dimethylformamide to form the WO 87/01283 A2 intermediate.
The WO 87/01283 A2 intermediate is then converted into rabeprazole through a series of chemical reactions.
The first step involves the treatment of the intermediate with HCl in the presence of a solvent such as acetonitrile to form the carboxylic acid.
This carboxylic acid is then treated with a base such as sodium hydroxide in the presence of a solvent such as water to form the sodium salt.
The resulting sodium salt is then treated with a reducing agent such as lithium aluminum hydride in the presence of a solvent such as ether to form the deoxygenated derivative.
The final step involves the treatment of the deoxygenated derivative with a base such as sodium hydroxide in the presence of a solvent such as water to form rabeprazole.
Simplified Method
The simplified method is a shorter and more efficient synthetic route for rabeprazole that involves the synthesis of the intermediate 2,2,2-trifluoroethyl 2-[(3,4-dichlorophenyl)methyl]acetate, also known as Intermediate A.
This intermediate is then transformed into rabeprazole through a series of chemical reactions.
The synthesis of Intermediate A begins with the reaction of 2,3-dichlorophenyl acetate with potassium carbonate in the presence of a solvent such as DMF or DMSO.
The resulting product is then treated with trifluoroethylamine in the presence of a solvent such as N,N-dimethylacetamide or N,N-dimethylformamide to form Intermediate A.
Intermediate A is then converted into rabeprazole through a series of chemical reactions.
The first step involves the treatment of Intermediate A with HCl in the presence of a solvent such as acetonitrile to form the carboxylic acid.
This carboxylic acid is then treated with a base such as sodium hydroxide in the presence of a solvent such as water to form the sodium salt.
The resulting sodium salt is then treated with a reducing agent such as lithium aluminum hydride in the presence of a solvent such as ether to form the deoxygenated derivative.
The final step involves the treatment of the deoxygenated derivative with a base such as sodium hydroxide in the presence of a solvent
