Paper
Synthesis of [benzyl‐7‐3H] and [benzoyl‐7‐14C] methyl 4‐(2,5‐dihydroxybenzylamino)benzoate
Published Feb 1, 1996 · G. F. Taylor, Maria K. Hristova-Kazmierski, F. Ley
Journal of Labelled Compounds and Radiopharmaceuticals
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Abstract
4-Amino[7-14C]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-dihydroxy-benzylimino)[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.
This method enables the synthesis of [benzyl-7-3H] and [benzoyl-7-14C] methyl 4-(2,5-dihydroxybenzylamino)benzoate, with potential applications in the field of radiopharmaceuticals.
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