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Rabeprazole is a proton pump inhibitor drug that is widely used in the treatment of acid-related stomach disorders such as gastroesophageal reflux disease (GERD), peptic ulcer disease, and Zollinger-Ellison syndrome.
It is also used to prevent gastric ulcer formation in patients undergoing long-term treatment with nonsteroidal anti-inflammatory drugs (NSAIDs).
Rabeprazole is available under various brand names, including Pariet, Pariet Plus, and Raebeprazine.
In the chemical industry, rabeprazole is synthesized through a series of chemical reactions that involve the transformation of raw materials into the final product.
The synthesis of rabeprazole involves several steps that require careful control and attention to detail to ensure the quality of the final product.
Step 1: Synthesis of 1-[(3S)-4-(4-Chloro-3-methyl-2-oxo-1,3-oxazolidin-3-yl)-3-hydroxyphenyl]-7,8-dihydroimidazo[1,2-d][1,4]benzoxazepine
The synthesis of rabeprazole begins with the synthesis of the compound 1-[(3S)-4-(4-Chloro-3-methyl-2-oxo-1,3-oxazolidin-3-yl)-3-hydroxyphenyl]-7,8-dihydroimidazo[1,2-d][1,4]benzoxazepine, which is a precursor to rabeprazole.
This compound is synthesized by a multi-step process that involves the transformation of a series of starting materials.
The synthesis of 1-[(3S)-4-(4-Chloro-3-methyl-2-oxo-1,3-oxazolidin-3-yl)-3-hydroxyphenyl]-7,8-dihydroimidazo[1,2-d][1,4]benzoxazepine begins with the synthesis of 4-chloro-3-methyl-2-oxo-1,3-oxazolidin-3-one.
This compound is synthesized by treating 3-methyl-2-oxo-1,3-oxazolidin-3-one with chloroacetone in the presence of a solvent such as dichloromethane.
The next step involves the synthesis of 3-hydroxyphenyl-4-chloro-3-methyl-2-oxo-1,3-oxazolidin-3-one by treating 4-chloro-3-methyl-2-oxo-1,3-oxazolidin-3-one with para-toluenesulfonylhydrazide in the presence of a solvent such as dichloromethane.
The next step involves the synthesis of 1-(3-hydroxyphenyl)-7,8-dihydroimidazo[1,2-d][1,4]benzoxazepine by treating 3-hydroxyphenyl-4-chloro-3-methyl-2-oxo-1,3-oxazolidin-3-one with methyl iodide in the presence of a solvent such as toluene.
Step 2: Synthesis of [1-(3S)-4-(4-Chloro-3-methyl-2-oxo-1,3-oxazolidin-3-yl)-3-hydroxyphenyl]-7,8-dihydroimidazo[1,2-d][1,4]benzoxazepine
The synthesis
