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Synthesis of C‐14 labeled Rac‐( 3R,2S )‐glycopyrronium bromide
Author(s) -
Bergare Jonas,
Nixon Neil,
Newsome Jeffery,
Thunberg Linda,
Elmore Charles S.
Publication year - 2020
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/jlcr.3864
Subject(s) - chemistry , decarboxylation , yield (engineering) , bromide , enantiomer , antagonist , pharmacokinetics , muscarinic acetylcholine receptor , chromatography , stereochemistry , pharmacology , combinatorial chemistry , organic chemistry , receptor , biochemistry , catalysis , medicine , materials science , metallurgy
In an effort to better understand the drug metabolism and pharmacokinetics (DMPK) properties of glycopyrronium bromide ( 1 ), a muscarinic acetylcholine receptor antagonist, a C‐14 labeled isotopologue was required. The compound was prepared in five synthetic steps and 5% overall radiochemical yield from Cu 14 CN. During the synthesis, an unexpected decarboxylation of phenylglyoxylate resulted in the loss of much of the radiolabeled compound. Chiral chromatography was utilized to isolate and deliver the proper pair of enantiomers as [ 14 C]‐1 .