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A Facile Synthesis of 2-Aminopropane-1,2,3-tricarboxylic Acid and Its Symmetrical Dimethyl Ester
Synthesis ( IF 2.2 ) Pub Date : 2021-08-10 , DOI: 10.1055/s-0040-1720389 Alexey V. Nizovtsev , Nicolai V. Bovin
中文翻译:
2-氨基丙烷-1,2,3-三羧酸及其对称二甲酯的简便合成
更新日期:2021-08-11
Synthesis ( IF 2.2 ) Pub Date : 2021-08-10 , DOI: 10.1055/s-0040-1720389 Alexey V. Nizovtsev , Nicolai V. Bovin
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.
中文翻译:
2-氨基丙烷-1,2,3-三羧酸及其对称二甲酯的简便合成
到2一个新的方便合成路线-氨基丙-1,2,3-三羧酸进行说明。三步合成的前两个阶段以一锅法进行,包括马尿酸与 DCC 的环化,然后用溴乙酸甲酯处理以产生烷基化的恶唑酮。其用HCl水解提供2 -氨基丙烷-1,2,3-三羧酸,为其HCl盐。在亚硫酰氯存在下用甲醇酯化所得酸选择性地产生其对称的二酯。