A Concise Synthetic Method for Constructing 3-Substituted Piperazine-2-Acetic Acid Esters from 1,2-Diamines

We report a short synthetic route for synthesizing 2,3-substituted piperazine acetic acid esters. Optically pure amino acids were efficiently converted into 1,2-diamines that could be utilized to deliver the title 2,3-substituted piperazines in five steps with a high enantiomeric purity. The novel r...

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Published inMolecules (Basel, Switzerland) Vol. 27; no. 11; p. 3419
Main Authors Chamakuri, Srinivas, Tang, Sunny Ann, Tran, Kevin A, Guduru, Shiva Krishna Reddy, Bolin, Peter K, MacKenzie, Kevin R, Young, Damian W
Format Journal Article
LanguageEnglish
Published Switzerland MDPI AG 25.05.2022
MDPI
Subjects
2,3-substituted piperazines
Acetic acid
Amino acids
annulation
Carbon
chiral piperazines
Chromatography
diamine
Diamines
Esters
masamune condensation
Piperazine
Substitutes
diamine
annulation
masamune condensation
2,3-substituted piperazines
chiral piperazines
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Summary:We report a short synthetic route for synthesizing 2,3-substituted piperazine acetic acid esters. Optically pure amino acids were efficiently converted into 1,2-diamines that could be utilized to deliver the title 2,3-substituted piperazines in five steps with a high enantiomeric purity. The novel route facilitated, for the first time, the synthesis of 3-phenyl substituted-2-piperazine acetic acid esters that were difficult to achieve using other methods; however, in this case, the products underwent racemization.
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ISSN:1420-3049
1420-3049
DOI:10.3390/molecules27113419