H. Abbas, L. Hankes, L. Feinendegen
Aug 1, 1990
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0
Influential Citations
2
Citations
Journal
Journal of Labelled Compounds and Radiopharmaceuticals
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.