Synthesis of [131I/123I]-2-[5-(4-iodophenyl)pentyl]oxirane-2- carboxylic acid ethyl ester.
A method is described for the synthesis, purification and radiolabelling of [123I/131I]2-[5-(4-iodophenyl)-pentyl]oxirane-2-carboxylic acid ethyl ester. For the synthesis of this new agent, 5-phenylpentyl bromide (1), synthesized by reacting 5-phenyl-1-pentanol with sodium bromide under acidic conditions, was converted to diethyl 5-phenylpentylmalonate (2), which, on alkaline hydrolysis, yielded ethyl 5-phenylpentylmalonate (3). Ethyl 7-phenyl-2-methyleneheptanoate (4), prepared from the monoester (3), was oxidized with m-chloroperbenzoic acid to yield ethyl 2-(5-phenylpentyl)oxirane-2-carboxylate 5. The method of radiolabelling, based on the thallation of compound (5) and the subsequent treatment with radioiodide, resulted in a regioselective radioiodination with a 54% radiochemical yield.
Abbas
H G
HG
Institute of Medicine, Research Centre, Jülich, F.R.G.
Younas
M
M
Feinendegen
L E
LE
D004852:Epoxy Compounds / Q000138:chemical synthesis*; D007004:Hypoglycemic Agents / Q000138:chemical synthesis*; D007457:Iodine Radioisotopes; D007553:Isotope Labeling / Q000379:methods*
D004852:Epoxy Compounds; D007004:Hypoglycemic Agents; D007457:Iodine Radioisotopes; C033891:ethyl 2-(5-(4-chlorophenyl)pentyl)oxiran-2-carboxylate