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Synthesis of morphine-[N-methyl-14C]-6-β-D-glucuronide

✍ Scribed by John R. Ferguson; Stephen J. Hollis; Grant A. Johnston; Keith W. Lumbard; Andrew V. Stachulski

Publisher
John Wiley and Sons
Year
2002
Tongue
French
Weight
95 KB
Volume
45
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

Protected morphine‐6‐glucuronide was converted into morphine‐[N‐methyl‐^14^C]‐6‐glucuronide by a three‐step procedure. Methyl (3‐pivaloylmorphin‐6‐yl 2,3,4‐tri‐O‐isobutyryl‐β‐D‐glucopyranosid)uronate was N‐demethylated by treatment with 1‐chloroethyl chloroformate to afford protected normorphine‐6‐glucuronide as its hydrochloride salt. The normorphine‐6‐glucuronide derivative was alkylated with iodomethane‐[^14^C] in the presence of potassium carbonate to produce C‐14 labelled protected morphine‐6‐glucuronide. Finally, hydrolysis of the protecting groups using 5% sodium hydroxide solution gave morphine‐[N‐methyl‐^14^C]‐6‐β‐D‐glucuronide with a specific activity of 41.8 mCi mmol^−1^ and radiochemical purity of 99.2% (HPLC). Copyright © 2002 John Wiley & Sons, Ltd.

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