The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: (S)-3-((S)-2-(((S)-1-Ethoxy-1-oxo-4-phenylbutan-2-yl)amino)propanoyl)-1-methyl-2-oxoimidazolidine-4-carboxylic acid hydrochloride, is researched, Molecular C20H28ClN3O6, CAS is 89396-94-1, about Studies on angiotensin converting enzyme inhibitors. V. The diastereoselective synthesis of 2-oxoimidazolidine derivatives, the main research direction is imidapril asym synthesis; enalapril diastereoselective synthesis; imidazolidinone derivative diastereoselective synthesis; angiotensin converting enzyme inhibitor imidapril.Application of 89396-94-1.
A diastereoselective synthesis of imidapril (I; R = H.HCl) (II), which is under clin. study as an antihypertensive drug based on its angiotensin converting enzyme (ACE)-inhibitory activity, was established. N-Alkylation of (2S)-2-amino-4-phenylbutyric acid Et ester with 3-((2R)-2-methane- or toluenesulfonyloxypropionyl)-2-oxoimidazolidine derivative III (R = Me, p-tolyl) diastereoselectively proceeded in an SN2 fashion to afford tert-Bu (4S)-3-[(2S)-2-[N-[(1S)-1-ethoxycarbonyl)-3-phenylpropyl]amino]propionyl]-1-methyl-2-oxoimidazolidine-4-carboxylate I (R = CMe3), a precursor of II. Alternatively benzyl (2S)-2-[N-[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]propionate IV, which is the key building block of I (R = CMe3), was synthesized by the same strategy. This procedure was also applied to the synthesis of enalapril.
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Reference:
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”