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-[ 18 F]-fluoronicotinate

Davis, Ryan A.; Fettinger, James C.

doi:10.1107/s2053229618005430

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-[ ¹⁸ F]-fluoronicotinate

Journal Article · Wed Apr 18 04:00:00 UTC 2018 · Acta Crystallographica. Section C, Structural Chemistry (Online)

DOI:https://doi.org/10.1107/s2053229618005430· OSTI ID:1541444

^[1]; Fettinger, James C.

DOE/OSTI

The synthesis, recrystallization, and X-ray deterimination of N, N,N-trimethyl-5-[(2,3,5,6-tetrafluorophenoxy)carbonyl]pyridin-2-aminium trifluoromethanesulfonate (PyTFP-precursor), C₁₅H₁₃F₄N₂O₂⁺·CF₃SO₃^-, is described. This triflate salt precursor is required for the synthesis of 2,3,5,6-tetrafluorophenyl 6-[¹⁸F]-fluoronicotinate ([¹⁸F]FPyTFP), a prosthetic group used to radiolabel peptides for positron emission tomography (PET), as peptides are increasingly being used as PET-imaging probes in nuclear medicine. Radiolabeling of peptides is typically done using a `prosthetic group', a small synthon to which the radioisotope is attached in the first step, followed by attachment to the peptide in the second step. During the synthesis of the PyTFP-precursor, displacement of a Cl atom with trimethylamine gas and anion replacement with a triflate counter-ion is critical, as incomplete replacement would hinder radioisotopic incorporation of nucleophilic fluorine-18 and result in diminished radiochemical yields. The structural determination of the PyTFP-precursor by X-ray crystallography helped confirm the anion exchange of chloride with triflate.

Research Organization:: Univ. of California, Davis, CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC)

DOE Contract Number:: SC0008385

OSTI ID:: 1541444

Journal Information:: Acta Crystallographica. Section C, Structural Chemistry (Online), Journal Name: Acta Crystallographica. Section C, Structural Chemistry (Online) Journal Issue: 5 Vol. 74; ISSN 2053-2296; ISSN ACSCGG

Publisher:: International Union of Crystallography

Country of Publication:: United States

Language:: English

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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-[ 18 F]-fluoronicotinate

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