Synthesis and determination for enantiomeric purity of 6-fluoro-L-DOPA
Tang, G.H.; Zhang, L.; Tang, X.L.; Wang, Y.X.; Yin, D.Z.
Yao Xue Xue Bao 36(10): 739-742
2001
ISSN/ISBN: 0513-4870 PMID: 12579971 Document Number: 531473
To study the synthesis and determination for enantiomeric purity of 6-fluoro-L-3, 4-dihydroxyphenylalanine (6-fluoro-L-DOPA, 6-FDOPA). 2-(2-Fluoro-4, 5-dimethoxybenzyl)-N-(diphenylmethylene) glycine tert-butyl ester (8), a new compound, was synthesized from the starting material nitroveratraldehyde via the nucleophilic displacement, reductive iodination, and chiral catalytic phase-transfer alkylation, and 6-FDOPA was prepared from hydrolysis of 8. The enantiomeric purity of 6-FDOPA was determined by HPLC method using a chiral mobil phase and reversed-phase C18 column. The total time of synthesis was less than 90 min, the overall chemical yield from potassium fluoride was about 33%, and the enantiomeric purity was above 95%. Large scale production of 6-FDOPA and automatic synthesis of 6-[18F]fluoro-L-DOPA with excellent chemical and entiomeric purity are available. The practical technique was provided for the radiochemical synthesis and entiomeric purity of 6-[18F]fluoro-L-DOPA.