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Synthesis of [benzyl‐7‐ 3 H] and [benzoyl‐7‐ 14 C] methyl 4‐(2,5‐dihydroxybenzylamino)benzoate
Author(s) -
Taylor George F.,
HristovaKazmierski Maria K.,
Ley F. Robert,
Kepler John A.
Publication year - 1996
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(199602)38:2<187::aid-jlcr832>3.0.co;2-3
Subject(s) - chemistry , benzoic acid , benzyl benzoate , sodium benzoate , methyl benzoate , yield (engineering) , tritium , sodium salt , ethyl benzoate , medicinal chemistry , organic chemistry , inorganic chemistry , catalysis , biochemistry , materials science , physics , nuclear physics , metallurgy
4‐Amino[7‐ 14 C]benzoic acid ( 3 ) is prepared by carbonation of the lithium salt of N, N‐bis(trimethylsilyl)aniline. The methyl ester ( 4 ) of 3 is generated with trimethylsilyldiazomethane, and 4 is coupled with 2,5‐dihydroxybenzaldehyde to yield methyl 4‐(2,5‐dihydroxybenzylimino)[7‐ 14 C]benzoate ( 5 ). 5 is reduced with sodium cyanoborohydride to give methyl 4‐(2,5‐dihydroxybenzylamino)[7‐ 14 C]‐benzoate with a specific activity of 38.9 mCi/mmol. Unlabeled 5 is reduced with tritium gas to give methyl 4‐(2,5‐dihydroxy[7‐ 3 H]‐benzylamino)benzoate with specific activity of 7.6 Ci/mmol.