AI Article Synopsis
- - A new method for creating a specific thiol-reactive compound, [ F]FPyME, was developed, improving the yield of its synthesis. - The synthesis involves a two-step one-pot procedure using a maleimide-containing nitro-precursor and a Diels-Alder adduct as starting materials. - The process includes nucleophilic radiofluorination and a heat-induced deprotection, achieving a 20% radiochemical yield in about 60 minutes, with the potential for creating similar compounds based on this technique.
Article Abstract
An improved high yielding radiosynthesis of the known thiol-reactive maleimide-containing prosthetic group1-[3-(2-[ F]fluoropyridine-3-yloxy)propyl]pyrrole-2,5-dione ([ F]FPyME) is described. The target compound was obtained by a two-step one-pot procedure starting from a maleimide-containing nitro-precursor that was protected as a Diels-Alder adduct with 2,5-dimethylfurane. Nucleophilic radiofluorination followed by heat induced deprotection through a Retro Diels Alder reaction yielded, after chromatographic isolation, [ F]FPyME with a radiochemical yield of 20% in about 60 min overall synthesis time. A variety of other [ F]fluoropyridine based maleimide-containing prosthetic groups should be accessible via the described synthetic strategy.
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