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Synthesis of 2-(5-(4-[123I/131I]iodophenyl)pentyl)-oxirane-2-carboxylic acid

✍ Scribed by Abbas H. G.; Hankes L. V.; Feinendegen L. E.

Publisher
John Wiley and Sons
Year
1990
Tongue
French
Weight
435 KB
Volume
28
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

A method is described for the synthesis, purification and radiolabelling of 2‐{5‐(4‐iodophenyl)pentyl}oxirane‐2‐carboxylic acid (I‐POCA). This new compound was synthesized from 5‐phenyl‐pentylbromide (1), prepared via 5‐phenyl‐1‐pentanol and subsequently converted to diethyl 5‐phenylpentylmalonate (2). The latter on alkaline hydrolysis yielded ethyl 5‐phenyl‐pentylmalonate (3). Para‐substitution of iodine on the phenyl moiety of the monoester (3) was accomplished by reacting compound (3) with thallium trifluoroacetate (TTFA) and subsequently with KI. Oxidation of ethyl 7‐(4‐iodophenyl)‐2‐methyleneheptanoate (5), which was synthesized from the monoester, ethyl 5‐(4‐iodophenyl)pentylmalonate (4) yielded ethyl 2‐{5‐(4‐iodophenyl)pentyl}oxirane‐2‐carboxylate (6). The radiolabelling procedure was based on a Cu(I)Cl‐assisted, isotopic exchange reaction, which produced a no‐carrier‐added and regiospecific radioiodination with a 32‐52% radiochemical yield.

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