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  • Title: [Synthesis and determination for enantiomeric purity of 6-fluoro-L-DOPA].
    Author: Tang GH, Zhang L, Tang XL, Wang YX, Yin DZ.
    Journal: Yao Xue Xue Bao; 2001 Oct; 36(10):739-42. PubMed ID: 12579971.
    Abstract:
    AIM: To study the synthesis and determination for enantiomeric purity of 6-fluoro-L-3, 4-dihydroxyphenylalanine (6-fluoro-L-DOPA, 6-FDOPA). METHODS: 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. RESULTS: 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%. CONCLUSION: 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.
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