Synthesis, characterization and radiolabelling of 2-[6-(4-bromophenoxy)hexyl]oxirane-2-carboxylic acid.
A method is described for the synthesis, purification and radiolabelling of 2-[6-(4-bromophenoxy)hexyl]-oxirane-2-carboxylic acid. For the synthesis of this new agent, 6-(4-bromophenoxy)hexylbromide (1), synthesized by the treatment of 4-bromophenol with 1,6-dibromohexane under basic conditions, was converted to diethyl 6-(4-bromophenoxy)hexylmalonate (2), which, on alkaline hydrolysis, yielded ethyl 6-(4-bromophenoxy)hexylmalonate (3). Ethyl 8-(4-bromophenoxy)-2-methyleneoctanoate (4), prepared from the monoester (3), was oxidized with m-chloroperbenzoic acid to yield ethyl 2-[6-(4-bromophenoxy)-hexyl]oxirane-2-carboxylate (5). The method of radiolabelling, based on the Cu(I)Cl-assisted nucleophilic exchange reaction, resulted in regioselective radiobromination with a 45% radiochemical yield.
Abbas
H G
HG
Institute of Medicine, Research Centre, Jülich, F.R.G.
Younas
M
M
Feinendegen
L E
LE
D001967:Bromine Radioisotopes; D004852:Epoxy Compounds / Q000138:chemical synthesis*; D007004:Hypoglycemic Agents / Q000138:chemical synthesis*; D007553:Isotope Labeling / Q000379:methods*
D001967:Bromine Radioisotopes; D004852:Epoxy Compounds; D007004:Hypoglycemic Agents; C054207:etomoxir