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Introduction:
Proton pump inhibitors (PPIs) are a class of drugs that are used to treat acid-related stomach disorders such as acid reflux, gastroesophageal reflux disease (GERD) and peptic ulcers.
Among the different PPIs, (-)-omeprazole is an important drug that is widely used in the treatment of acid-related disorders.
In this article, we will discuss the instructions for preparing (-)-omeprazole in the chemical industry.
Preparation of (-)-Omeprazole:
The preparation of (-)-omeprazole involves several steps, including the synthesis of the intermediate compound, 1-[[(2S)-2-(difluoromethyl)-1,4-oxazepin-3-yl]amino]-3-[(2,4-dichlorophenyl)methyl]-urea, followed by the resolution of the resulting racemate to obtain the pure (-)-enantiomer.
Step 1: Synthesis of 1-[[(2S)-2-(difluoromethyl)-1,4-oxazepin-3-yl]amino]-3-[(2,4-dichlorophenyl)methyl]-urea:
To prepare 1-[[(2S)-2-(difluoromethyl)-1,4-oxazepin-3-yl]amino]-3-[(2,4-dichlorophenyl)methyl]-urea, the following reagents and chemicals are needed: 3-[[(2S)-2-(difluoromethyl)-1,4-oxazepin-3-yl]amino]-N-[[2,4-dichlorophenyl)methyl]acetamide, hydroxyquinoline, and sodium hydroxide.
The first step in the synthesis of 1-[[(2S)-2-(difluoromethyl)-1,4-oxazepin-3-yl]amino]-3-[(2,4-dichlorophenyl)methyl]-urea is the preparation of the starting material, 3-[[(2S)-2-(difluoromethyl)-1,4-oxazepin-3-yl]amino]-N-[[2,4-dichlorophenyl)methyl]acetamide.
This is done by reacting N-[(2S)-2-(difluoromethyl)-1,4-oxazepin-3-yl]acetamide with 2,4-dichlorophenyl isocyanate in the presence of a catalytic amount of pyridine.
The next step is the reaction of the resulting intermediate with hydroxyquinoline in the presence of sodium hydroxide, which leads to the formation of 1-[[(2S)-2-(difluoromethyl)-1,4-oxazepin-3-yl]amino]-3-[(2,4-dichlorophenyl)methyl]-urea.
Step 2: Resolution of 1-[[(2S)-2-(difluoromethyl)-1,4-oxazepin-3-yl]amino]-3-[(2,4-dichlorophenyl)methyl]-urea:
To prepare the pure (-)-enantiomer of 1-[[(2S)-2-(difluoromethyl)-1,4-oxazepin-3-yl]amino]-3-[(2,4-dichlorophenyl)methyl]-urea, the racemate obtained from the synthesis of 1-[[(2S)-2-(difluoromethyl)-
