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Synthesis of N‐(2‐[ 18 F]fluoroethyl)‐N′‐methylthiourea: a hydrogen peroxide scavenger
Author(s) -
Gilissen C.,
Bormans G.,
de Groot T.,
Verbruggen A.
Publication year - 1998
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/(sici)1099-1344(199806)41:6<491::aid-jlcr102>3.0.co;2-9
Subject(s) - chemistry , scavenger , hydrogen peroxide , yield (engineering) , nuclear chemistry , fluoride , isothiocyanate , phthalimide , hydrazide , hydrazine (antidepressant) , nucleophilic substitution , high performance liquid chromatography , fluorine , medicinal chemistry , radical , organic chemistry , chromatography , inorganic chemistry , materials science , metallurgy
N‐(2‐[ 18 F]fluoroethyl)‐N′‐methylthiourea ([ 18 F]FEMTU), a fluorine‐18 labelled derivative of the hydrogen peroxide scavenger dimethlthiourea (DMTU), has been synthesized by reaction of 2‐[ 18 F]fluoroethylamine with methylisothiocyanate. 2‐[ 18 F]Fluoroethylamine was obtained in modest radiochemical yields (39±6%, mean±sd, n=5, decay corrected) by nucleophilic substitution with [ 18 F]fluoride on N‐[2‐( p ‐toluenesulfonyloxy)ethyl]phthalimide followed by deprotection with hydrazine and distillation. The distilled 2‐[ 18 F]fluoroethylamine was trapped in CH 2 Cl 2 and reacted with methyl‐isothiocyanate to yield [ 18 F]FEMTU that was purified by reversed phase HPLC. The total synthesis takes 150 min and provides [ 18 F]FEMTU with a specific activity of 3.3±0.5 GBq/μmol (mean±sd, n=3) at end of synthesis, with an overall decay corrected radiochemical yield of 25±8% (mean±sd, n=5). © 1998 John Wiley & Sons, Ltd.