What is it about?
A crystal structure of the N,N,N-Trimethyl-5-[(2,3,5,6-tetrafluorophenoxy)carbonyl]pyridin-2-aminium trifluoromethanesulfonate precursor was obtained to show that the counter anion of chloride was replaced with a trifluoromethanesulfonate anion.
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Why is it important?
This work illustrates that anion replacement of a chloride can be achieved via reaction with trimethylsilyl trifluoromethanesulfonate a crucial step in the synthesis of the N,N,N-trimethyl-5-[(2,3,5,6-tetrafluorophenoxy) carbonyl]pyridin-2-aminium trifluoromethanesulfonatetetrafluorophenylester precursor synthesis, because the subsequent radioisotopic incorporation of fluorine-18 would fail if remaining amounts of chloride are present. Radiolabeling of molecules/biomolecules can be challenging and providing alternative means to achieve good radioisotopic incorporation and radiolabeling yields can provide an avenue to explore questions in biology and disease by positron detection.
Perspectives
I hope this article will help others with chemistry associated with developing other prosthetic groups used to radiolabel molecules with fluorine-18 and provide confidence in the synthesis and use of N,N,N-trimethyl-5-[(2,3,5,6-tetrafluorophenoxy)carbonyl]pyridin-2-aminium trifluoromethanesulfonate trimethylaminium nicotinic tetrafluorophenylester precursor used to generate the radioactive [18F]-fluoronicotinic tetrafluorphenyl ester prosthetic group. Hopefully an increase in use of this prosthetic group will stem from this publication.
Ryan Davis
University of California, Davis
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This page is a summary of: N,N,N-Trimethyl-5-[(2,3,5,6-tetrafluorophenoxy)carbonyl]pyridin-2-aminium trifluoromethanesulfonate a precursor for the synthesis of 2,3,5,6-tetrafluorophenyl 6-[18F]-fluoronicotinate, Acta Crystallographica Section C Structural Chemistry, April 2018, International Union of Crystallography,
DOI: 10.1107/s2053229618005430.
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