三氟甲磺酸
合成子
化学
三甲胺
亲核细胞
药物化学
硫
醛
氯化物
立体化学
盐(化学)
有机化学
催化作用
作者
Ryan A. Davis,James C. Fettinger
标识
DOI:10.1107/s2053229618005430
摘要
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), C 15 H 13 F 4 N 2 O 2 + ·CF 3 SO 3 − , is described. This triflate salt precursor is required for the synthesis of 2,3,5,6-tetrafluorophenyl 6-[ 18 F]-fluoronicotinate ([ 18 F]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.
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