A convenient and new approach to the synthesis of ω-heterocyclic amino acids from carboxy lactams through ring-chain-transformation. Part 2: Synthesis of (2R)-/(2S)-2-aminomethyl-3-(1-aryl-/1,5-diaryl-1H-pyrazol-3-yl)-propionic acid |
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| Authors: | Rakesh K Singh Neelima Sinha Sanjay Jain Mohammad Salman Nitya Anand |
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| Institution: | a Medicinal Chemistry Division, New Drug Discovery Research, Ranbaxy Laboratories Limited, R&D II, Plot # 20, Sector-18, Udyog Vihar Industrial Area, Gurgaon 122 001, India
b Department of Chemistry, Jamia Millia Islamia, New Delhi 110 015, India |
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| Abstract: | Making use of amide activation, a convenient and short path synthesis of optically pure ω-heterocyclic-β-amino acids has been achieved from (1R,3R)- and (1R,3S)-5-oxo-1-(1-phenyl-ethyl)-pyrrolidine-3-carboxylic acid methyl ester. The key step of the synthesis involves a regiospecific ring-chain-transformation of the enaminones when subjected to 1,2-binucleophilic attacks. The method is illustrated by the synthesis of (2R)-/(2S)-2-aminomethyl-3-(1-aryl-/1,5-diaryl-1H-pyrazol-3-yl)-propionic acid. |
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| Keywords: | Unnatural β-amino acids 2-Aminomethyl-3-(substituted-1H-pyrazol-3-yl)-propionic acid Chirality Ring-chain-transformation reaction Sulfur extrusion reaction Hydrogenation |
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