One-pot esterification and amidation of phenolic acids

TETRAHEDRON

卷:70

Article

Nakamura, Kozo^1,2,3  Nakajima, Takero⁴  Aoyama, Toshifumi⁴  Okitsu, Sho²  Koyama, Masahiro³ 

[1] Shinshu Univ, Inst Agr, Acad Assembly, Minamiminowa, Nagano 3994598, Japan

[2] Shinshu Univ, Grad Sch Agr, Dept Biosci & Biotechnol, Minamiminowa, Nagano 3994598, Japan

[3] Shinshu Univ, Fac Agr, Dept Biosci & Biotechnol, Minamiminowa, Nagano 3994598, Japan

[4] Shinshu Univ, Grad Sch Med, Inst Pathogenesis & Dis Prevent, Dept Metab Regulat, Matsumoto, Nagano 3908621, Japan

关键词: Esters;    Amides;    Phenolic acids;    Caffeic acid phenethyl esters isotopomers;   

DOI  :  10.1016/j.tet.2014.08.028

来源: Elsevier

【 摘 要 】

We developed a new one-pot reaction of phenolic acids to afford the corresponding esters and amides through acyl-protected and activated phenolic acid intermediates. The simultaneous protection/activation of phenolic acids with alkylchloroformates proceeded readily in the presence of DMAP at room temperature; subsequent addition of alcohols or amines afforded the corresponding esters or amides. The use of iso-butyloxycarbonyl as the protecting and activating group in the one-pot reactions afforded phenolic esters or amides in 91% average yield. As a practical example of this convenient synthesis, caffeic acid phenethyl ester (CAPE) was readily synthesized from commercially available caffeic acid and phenethyl alcohol in 95% yield, and an isotopomer of CAPE, [3,10-C-13(2)]CAPE, was synthesized in 91% yield from [3-C-13]caffeic acid and 2-[1-C-13]phenethyl alcohol. This method may be useful for the convenient esterification and amidation of diverse phenolic acids. (C) 2014 Elsevier Ltd. All rights reserved.

【 授权许可】

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