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Robust and General Procedure for Carbon Isotope Labeling of Linear Urea Derivatives with Carbon Dioxide

preprint
submitted on 04.01.2021, 21:24 and posted on 06.01.2021, 04:49 by Victor Babin, Antoine Sallustrau, Olivier Loreau, Fabien Caillé, Amélie Goudet, Héloïse Cahuzac, Antonio Del Vecchio, Frédéric Taran, Davide Audisio
Carbon isotope labeling is a traceless technology, which allows tracking the fate of organic compounds either in the environment or in living organisms. Despite recent advances in the field, the development of robust and general technologies remains a significant task. This full article reports on a general approach to label urea derivatives with all carbon isotopes, including 14C and 11C. Based on a Staudinger aza-Wittig sequence, it provides access to all aliphatic/aromatic urea combinations as well as to semicarbazides, sulfonylureas, hydroxyl ureas, and simple terminal ureas. A de-risking approach was developed to evaluate the robustness of the reaction. This technology is based on [14C]CO2 screening that allowed to investigate the tolerance of the procedure with most representative heterocycles and functional groups found in FDA approved drugs.

History

Email Address of Submitting Author

davide.audisio@cea.fr

Institution

CEA, DRF/JOLIOT/SCBM

Country

France

ORCID For Submitting Author

0000-0002-6234-3610

Declaration of Conflict of Interest

No

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