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The Synthetic Routes of tert-Butyl [(1R,2S,5S)-2-amino-5-[(dimethylamino)c]-1,3-oxazepane-6-carboxylate: A Comprehensive Review
In the world of chemical synthesis, the tert-butyl [(1R,2S,5S)-2-amino-5-[(dimethylamino)c]-1,3-oxazepane-6-carboxylate molecule has garnered significant interest due to its unique properties and potential applications.
This molecule is a synthetic intermediate that can be used in the production of various chemicals, pharmaceuticals, and agrochemicals.
The synthetic route to this molecule can be divided into several steps, which involve the use of various chemical reactions and reaction conditions.
In this article, we will provide an overview of the different synthetic routes that have been reported in the literature for the synthesis of tert-butyl [(1R,2S,5S)-2-amino-5-[(dimethylamino)c]-1,3-oxazepane-6-carboxylate.
Step 1: Preparation of N-(tert-Butyl)-N-(dimethylamino)acetamide
The first step in the synthesis of tert-butyl [(1R,2S,5S)-2-amino-5-[(dimethylamino)c]-1,3-oxazepane-6-carboxylate involves the preparation of N-(tert-Butyl)-N-(dimethylamino)acetamide.
This intermediate can be synthesized by reacting tert-butylamine with dimethylamine in the presence of a suitable solvent such as methanol or ethanol.
The reaction is typically carried out at room temperature with the addition of a catalyst such as pyridine.
Step 2: Reduction of N-(tert-Butyl)-N-(dimethylamino)acetamide to N-(tert-Butyl)-N-(dimethylamino)methanamine
The next step is the reduction of N-(tert-Butyl)-N-(dimethylamino)acetamide to N-(tert-Butyl)-N-(dimethylamino)methanamine.
This reduction can be achieved by using various reagents such as lithium aluminum hydride (LiAlH4), hydrogen in the presence of a catalyst such as palladium on barium sulfate, or sodium borohydride.
The reduction reaction is typically carried out in the presence of a solvent such as ethanol or ether.
Step 3: N-(tert-Butyl)-N-(dimethylamino)methanamine to N-(tert-Butyl)-N-[(1R,2S,5S)-5-(dimethylamino)-1,3-oxazepin-2-yl]-methanamine
The next step is the conversion of N-(tert-Butyl)-N-[(1R,2S,5S)-5-(dimethylamino)-1,3-oxazepin-2-yl]-methanamine, which can be achieved by reacting N-(tert-Butyl)-N-[(1R,2S,5S)-5-(dimethylamino)-1,3-oxazepin-2-yl]-methanamine with (R)-1-[[(1S,2R)-1,2-diamino-2-(4,8-dimethyl-2H-imidazo[1,2-d][1,4]benzoxazepin-9-yl)amino]carbonyl]-4-methyl-7-oxo-6-[(phenylamino)carbonyl]-5-pyrimidinecarboxylic acid.
This reaction is typically carried out in the presence of a solvent such as DMF or N,N-dimethylacetamide and a catalyst such as 4DMAP or HOBT.
Step 4: N-(tert-Butyl)-N-[(1R,2S,5S)-5-(dimethylamino)-1,3-oxazepin-2-yl]