Synthesis of [Benzyl-7-3H] and [Benzoyl-7-14C] Methyl 4-(2,5-Dihydroxybenzylamino)benzoate
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‐dihydroxybenzylimino)[7‐14C]benzoate (5). 5 is reduced with sodium cyanoborohydride to give methyl 4‐(2,5‐dihydroxybenzylamino)[7‐14C]‐benzoate with a specific activity of 38.9 mCi/mmol. Unlabeled 5 is reduced with tritium gas to give methyl 4‐(2,5‐dihydroxy[7‐3H]‐benzylamino)benzoate with specific activity of 7.6 Ci/mmol.
Taylor, G., Hristova-Kazmierski, M., Ley, F., & Kepler, J. (1996). Synthesis of [Benzyl-7-3H] and [Benzoyl-7-14C] Methyl 4-(2,5-Dihydroxybenzylamino)benzoate. Journal of Labelled Compounds and Radiopharmaceuticals, 38(2), 187-192. https://doi.org/10.1002/(SICI)1099-1344(199602)38:23.0.CO;2-3