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• W2099016712 abstract "The ¹⁸F-labeled aromatic amino acid 6-fluoro-3,4-dihydroxy-l-phenylalanine (6-¹⁸F-fluoro-l-DOPA) is widely used as a radiopharmaceutical in neurologic and oncologic PET. In this study, a novel approach to the preparation of carrier-added (CA) 6-¹⁸F-fluoro-l-DOPA in 3 radiosynthesis steps was developed and evaluated; in this approach, direct nucleophilic ¹⁸F fluorination of a protected amino acid derivative was used. The method currently used for the routine preparation of 6-¹⁸F-fluoro-l-DOPA by electrophilic labeling is limited to the production of small amounts of activity at high costs. Alternative syntheses based on the advantage of large-scale production of nucleophilic ¹⁸F-fluoride, however, either have resulted in insufficient enantiomeric purity or are difficult to automate because of the complexity of the necessary multiple steps. <b>Methods:</b> An isotopic exchange reaction on the precursor (2<i>S</i>,5<i>S</i>)-<i>tert</i>-butyl-5-(4-benzyloxy-2-fluoro-5-formylbenzyl)-2-<i>tert</i>-butyl-3-methyl-4-oxoimidazolidine-1-carboxylate was used. The formyl group served as the activating group in the ¹⁸F-for-¹⁹F exchange with tetrabutylammonium bicarbonate for anion activation in <i>N,N</i>-dimethylformamide. The intermediate was converted to a hydroxy group by Baeyer–Villiger oxidation with <i>meta</i>-chloroperbenzoic acid. After final deprotection with hydrobromic acid, CA 6-¹⁸F-fluoro-l-DOPA was isolated by high-performance liquid chromatography. <b>Results:</b> The precursor was obtained by an 11-step organic synthesis. The optimized isotopic ¹⁸F exchange proceeded with a radiochemical yield of about 50%. The complete preparation and isolation of CA 6-¹⁸F-fluoro-l-DOPA thus far are possible with a radiochemical yield of about 22%, within a synthesis time of 105 min, and at a much higher specific activity than with the electrophilic method. The enantiomeric excess of the desired l-isomer was greater than 96%.<b>Conclusion:</b> The pathway to 6-¹⁸F-fluoro-l-DOPA by isotopic exchange not only is more efficient but also is suited to automation as a “one-pot” procedure." @default.
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• W2099016712 date "2009-09-16" @default.
• W2099016712 modified "2023-09-26" @default.
• W2099016712 title "Three-Step, “One-Pot” Radiosynthesis of 6-Fluoro-3,4-Dihydroxy-l-Phenylalanine by Isotopic Exchange" @default.
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• W2099016712 doi "https://doi.org/10.2967/jnumed.109.063297" @default.
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