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Synthesis of highly pure 14C-labelled DL-allantoin and 13C NMR analysis of labelling integrity

✍ Scribed by Simon G. Patching

Publisher
John Wiley and Sons
Year
2009
Tongue
French
Weight
124 KB
Volume
52
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

A number of synthetic approaches are assessed to prepare allantoin labelled with ^14^C given certain requirements and technical limitations. A method that fulfils these criteria is described to achieve the synthesis of highly pure ^14^C‐labelled allantoin with the label introduced to the ureido carbonyl group in the final step by reaction of 5‐chlorohydantoin with [^14^C]urea. The chosen method favours high purity at the expense of radiochemical yield, which is achieved at a level of 8%. The integrity of the label is then investigated by performing an NMR analysis of ^13^C‐labelled allantoin synthesized by the same method. The ^13^C NMR spectrum confirms partial scrambling of the label to the C‐2 position by equilibration of the product via a putative bicyclic intermediate, which had been suggested by other workers. The ^14^C‐labelled allantoin synthesized by this method is therefore assigned as DL‐[H~2~N^14^CO/^14^C‐2]allantoin. This study also includes the first full characterization of a side product, 5‐hydroxy‐5‐methoxyhydantoin, obtained by the reaction of a 5‐hydroxyhydantoin intermediate with the methanol solvent. Copyright © 2009 John Wiley & Sons, Ltd.

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