Synthesis of [l-3H]morphine-6-beta-D-glucuronide
Berrang, B., Wyrick, C., Carroll, F., & Seltzman, H. (1999). Synthesis of [l-3H]morphine-6-beta-D-glucuronide. Journal of Labelled Compounds and Radiopharmaceuticals, 42(9), 851-857.
Tritiated morphine of high specific activity was protected at the 3-position by acetylation and subjected to glucuronidation by Koenigs-Knorr procedure with methyl 2,3,4-tri-0-acetyl-1-bromo-1-deoxy-D-glucopyranuronate and silver carbonate. Fully protected morphine-6-glucuronide was obtained in 42% yield and 95% radiochemical purity as determined by TLC-RAM. Alkali catalyzed solvolysis in two steps furnished [1-H-3]morphine-6-beta-D-glucuronide in 23% overall radiochemical yield and 99% radiochemical purity determined by HPLC - liquid scintillation counting and TLC-RAM.