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Synthesis 2021; 53(23): 4428-4432
DOI: 10.1055/s-0040-1720389
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A Facile Synthesis of 2-Aminopropane-1,2,3-tricarboxylic Acid and Its Symmetrical Dimethyl Ester

Alexey V. Nizovtsev∗
,
Nicolai V. Bovin
This work was funded by the Russian Foundation for Basic Research (Project No. 19-03-00477). The IBCH core facility (CKP IBCH) was supported by Ministry of Education and Science of the Russian Federation (grant RFMEFI62117X0018).
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Abstract

A new convenient synthetic route to 2-aminopropane-1,2,3-tricarboxylic acid is described. The first two stages of the three-step synthesis are performed in a one-pot procedure and include the cyclization of hippuric acid with DCC followed by treatment with methyl bromoacetate to yield an alkylated oxazolone. Its hydrolysis with HCl provides 2-aminopropane-1,2,3-tricarboxylic acid as its HCl salt. Esterification of the resulting acid with methanol in the presence of thionyl chloride leads selectively to its symmetrical diester.

Key words

alkylation - cyclization - esterification - oxazolone - amino acids­

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1720389.
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Publication History

Received: 31 May 2021

Accepted after revision: 05 July 2021

Article published online:
10 August 2021

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