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Synthesis and Cu 1+ Assisted radiosynthesis of 2‐radioiodo phloretinic acid, a potential glut tracer
Author(s) -
Mertens J.,
Boumon R.,
Steegmans P.
Publication year - 2001
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/jlcr.25804401334
Subject(s) - radiosynthesis , chemistry , yield (engineering) , benzoic acid , labelling , nucleophile , halogenation , radiochemistry , copper , substrate (aquarium) , nuclear chemistry , medicinal chemistry , combinatorial chemistry , organic chemistry , catalysis , biochemistry , materials science , oceanography , microbiology and biotechnology , in vivo , metallurgy , biology , geology
2‐Bromo‐phloretinic acid (2‐Br‐PLA): 2‐bromo‐4‐(3‐oxo‐3(2,4,6‐trihydroxyphenyl) propyl)benzoic acid, the precursor molecule for the radiosynthesis of 2‐radioiodophloretinic acid (2‐*I‐PLA): 2‐radioiodo‐4‐(3‐oxo‐3(2, 4, 6‐trihydroxyphenyl)‐propyl)benzoic acid, was prepared by a twelve step synthesis starting from hydrocinnamic acid. The radiosynthesis was carried out by applying the Cu(I)‐assisted nucleophilic non‐isotopic exchange reaction in acidic reducing medium. The amount of copper to reach high yields was found to be critical. At substrate to copper ratios generally used in this type of synthesis dehalogenation of the starting compound occurred, decreasing the labelling yield considerably. In optimal conditions a labelling yield of 95% was reached.