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Methodes de Synthese de l'Acide Agarique Racemique Marque au 14 C (acide α‐cetyl citrique (carboxyle‐1 14 C) OU acide hydroxy‐2 nonadecanetricarboxylique‐1,2 (carboxyle 14 CO)‐3)
Author(s) -
Lellouche J. P.,
Beaucourt J. P.,
Pichat L.
Publication year - 1984
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580210205
Subject(s) - chemistry , saponification , yield (engineering) , medicinal chemistry , ethyl bromoacetate , diazomethane , nuclear chemistry , hydrogen peroxide , organic chemistry , materials science , metallurgy
Racemic [3‐carboxyl 14 C] agaric acid triethyl ester was prepared in low yield by treatment of ethyl 2‐ethoxalyl octadecanoate 2 with either ethyl lithioacetate or ethyl bromoacetate, zinc and methyl borate. In another approach, lithio ethynyltrimethylsilane 6 was condensed with 2 to give 7 which, with dicyclohexylborane 8 , gave the vinyl borane 9 ; the latter, by hydrogen peroxide oxidation followed by reaction of diazomethane gave the mixed ester 11 in low yield. [3‐carboxyl 14 C] Agaric acid, specific activity 57 mCi/mmol, was obtained from 5 or 11 by saponification with lithium hydroxide in 1,2‐dimethoxyethane. The best overall yield from ethyl [1‐ 14 C] stearate was 18%.