Process for the preparation of tert-Butyl [(1R,2S,5S)-2-azido-5- [(dimethylamino)carbonyl]cyclohexyl]carbamate
Publication Date: 2016-Apr-21
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Process for the preparation of tert-Butyl [(1R,2S,5S)-2-azido-5-
referred to herein as compound 1, may be an intermediate in the preparation of N-(5- Chloropyridin-2-yl)-N'-[(1S,2R,4S)-4-[(dimethylamino)carbonyl]-2-[[(5-methyl-4,5,6,7- tetrahydrothiazolo[5,4-c]pyridin-2-yl)carbonyl]amino]cyclohexyl]ethanediamide, 4- methylbenzenesulfonate monohydrate (referred to as compound A).
Compound 1 was prepared in four steps (with or without isolation) from (1S,3R,4R)-(+)-3-[(tert- Butoxycarbonyl)amino]-4-hydroxycyclohexane carboxylic acid ethyl ester (referred to as compound 2).
In the first step, the compound 2 was treated with mesyl chloride in a solvent such as ethyl acetate, dichloromethane, methyl isobutyl ketone or toluene, in the presence of a base such as Triethylamine, N, N-diisopropyl ethyl amine or N-methyl morpholine at ambient temperature. After completion of reaction, resultant compound, ethyl (1S,3R,4R)-3-((tert- butoxycarbonyl)amino)-4-((methylsulfonyl) oxy)cyclohexane-1-carboxylate (referred to as compound 3) is extracted in a suitable solvent.
In the second step, the compound 3 was subsequently treated with sodium azide in the presence of a catalyst such as Benzyltriethylammonium chloride (TEBAC), tetrabutyl ammonium chloride, Docecyl pyridinium chloride or tetrabutyl ammonium acetate, to obtain the compound, (1S,3R,4S)-(+)-4-Azi...