A three-step radiosynthesis of 6-[18 F]fluoro-L-meta-tyrosine starting with [18 F]fluoride
The radiosynthesis of 6‐[18 F]fluoro‐L‐m‐tyrosine has generally been performed by electrophilic radiofluorination, which exhibits several drawbacks. In the present work, a three‐step radiochemical synthesis is described starting from [18 F]fluoride. The synthetic sequence, including isotopic exchang...
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Published in | Journal of labelled compounds & radiopharmaceuticals Vol. 58; no. 3; pp. 133 - 140 |
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Main Authors | , , |
Format | Journal Article |
Language | English French German |
Published |
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Blackwell Publishing Ltd
01.03.2015
Wiley Wiley Subscription Services, Inc |
Subjects | |
Online Access | Get full text |
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Summary: | The radiosynthesis of 6‐[18 F]fluoro‐L‐m‐tyrosine has generally been performed by electrophilic radiofluorination, which exhibits several drawbacks. In the present work, a three‐step radiochemical synthesis is described starting from [18 F]fluoride. The synthetic sequence, including isotopic exchange, Baeyer–Villiger oxidation, and hydrolysis, were examined comparing four fluorobenzophenone derivatives as labeling precursors. Of those, (2S,5S)‐tert‐butyl 5‐(5‐acetyl‐2‐fluorobenzyl)‐2‐tert‐butyl‐3‐methyl‐4‐oxoimidazolidine‐1‐carboxylate (1a) and (2S,5S)‐tert‐butyl 2‐tert‐butyl‐5‐(2‐fluoro‐5‐(2,2,2‐trifluoroacetyl)benzyl)‐3‐methyl‐4‐oxoimidazolidine‐1‐carboxylate (1d) proved to be the most suitable ones. 6‐[18 F]Fluoro‐L‐m‐tyrosine was obtained with overall radiochemical yields of 8–13% and an enantiomeric excess of up to 98%.
The radiosynthesis of 6‐[18 F]fluoro‐L‐m‐tyrosine has generally been performed by electrophilic radiofluorination, which exhibits several drawbacks. In the present work, a three‐step radiochemical synthesis is described starting from [18F]fluoride. The synthetic sequence, including isotopic exchange, Baeyer‐Villiger oxidation, and hydrolysis, were examined comparing four fluorobenzophenone derivatives as labeling precursors. [18F]fluoro‐L‐m‐tyrosine was obtained with overall radiochemical yields of 8–13% and an enantiomeric excess of up to 98%. |
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Bibliography: | istex:3446EC3739F7D1C548AB6E94817FF09F8E00BF7F ark:/67375/WNG-N09HT9CF-9 Dedicated to Prof. Dr. Bengt Långström, with deepest appreciation, to celebrate his outstanding life-long contribution to the field of radiochemistry and on the occasion of his retirement as editor of the Journal of Labelled Compounds and Radiopharmaceuticals. ArticleID:JLCR3273 This article is published in Journal of Labelled Compounds and Radiopharmaceuticals as a special issue on 'Bengt Långström', edited by Antony Gee, Department of Chemistry and Biology, Division of Imaging Sciences and Bioengineering, Kings College London, UK and Albert Windhorst, Department of Radiology and Nuclear Medicine, VU University Medical Center, Amsterdam, The Netherlands. This article is published in Journal of Labelled Compounds and Radiopharmaceuticals as a special issue on ‘Bengt Långström’, edited by Antony Gee, Department of Chemistry and Biology, Division of Imaging Sciences and Bioengineering, Kings College London, UK and Albert Windhorst, Department of Radiology and Nuclear Medicine, VU University Medical Center, Amsterdam, The Netherlands. Dedicated to Prof. Dr. Bengt Långström, with deepest appreciation, to celebrate his outstanding life‐long contribution to the field of radiochemistry and on the occasion of his retirement as editor of the Journal of Labelled Compounds and Radiopharmaceuticals. ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 0362-4803 1099-1344 |
DOI: | 10.1002/jlcr.3273 |