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No-carrier-added asymmetric synthesis of α-methyl-α-amino acids labelled with fluorine-18

par Damhaut, Philippe;Lemaire, Christian;Plenevaux, Alain;Brihaye, Claude ;Christiaens, Léon;Comar, Dominique
Référence Tetrahedron, 53, 16, page (5785-5796)
Publication Publié, 1997-04

Article révisé par les pairs

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Résumé :

Various [18F]fluoro aromatic α-methyl-L-amino acids T1 have been synthesized with high enantiomeric purity (ee > 97%). These new radiopharmaceuticals for Positron Emission Tomography (PET), potential inhibitors of enzymatic functions, were regiospecifically labelled by nucleophilic substitution on trimethylammoniumbenzaldehyde triflate precursors 9. The [18F]fluoro aromatic aldehydes 12 obtained were easily converted to the corresponding [18F]fluorobenzyl halides [13 (X = I)]. After alkylation of the lithium enolate of (2S,5S)-1-tert-Boc-2-tert-butyl-3,5-dimethyl-imidazolin-4-one 2, the adduct were cleaved to give, after HPLC purification, various [18F]fluoro-α-methyl amino acid analogs with radiochemical yields of 10% (End of Bombardment, EOB) after a synthesis time of 120 min. The corresponding [19F]fluorinated amino acids 4 and [19F]fluoro intermediates were also prepared.