An Improved Synthesis of Homocitrate

Autor: Ji-Qing Xu, Zeng-Chun Li
Jazyk: angličtina
Rok vydání: 1998
Předmět:
Zdroj: Molecules, Vol 3, Iss 2, Pp 31-34 (1998)
Druh dokumentu: article
ISSN: 1420-3049
DOI: 10.3390/30200031
Popis: Monoethyl malonate (1) and tert-butyl alcohol are esterified by catalysis with dicyclohexylcarbodiimide and 4-dimethylaminopyridine to yield ethyl t-butyl malonate (2). The ethoxymagnesio derivative (3) of the ester is condensed with b-carbomethoxypropionyl chloride to give the triester (4), which is decomposed by heating under vacuum in the presence of b-naphthalensulfonic acid to give ethyl methyl β-ketoadipate (5). Compound 5 is reacted with hydrogen cyanide,followed by hydrolysis of the cyanohydrin to give the free acid (6). Compound 6 is converted to homocitrate (7) by the use of an improved procedure.
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