Synthesis and Reactivity of 18F-Labeled α,α-Difluoro-α-(aryloxy)acetic Acids

Tanatorn Khotavivattana; Samuel Calderwood; Stefan Verhoog; Lukas Pfeifer; Sean Preshlock; Neil Vasdev; Thomas L Collier; Véronique Gouverneur

doi:10.1021/acs.orglett.6b03730

Synthesis and Reactivity of ¹⁸F-Labeled α,α-Difluoro-α-(aryloxy)acetic Acids

Org Lett. 2017 Feb 3;19(3):568-571. doi: 10.1021/acs.orglett.6b03730. Epub 2017 Jan 13.

Authors

Tanatorn Khotavivattana¹, Samuel Calderwood¹, Stefan Verhoog¹, Lukas Pfeifer¹, Sean Preshlock¹, Neil Vasdev^{2

3}, Thomas L Collier^{2

3

4}, Véronique Gouverneur¹

Affiliations

¹ Chemistry Research Laboratory, University of Oxford , Mansfield Road, Oxford OX1 3TA, U.K.
² Division of Nuclear Medicine and Molecular Imaging, Massachusetts General Hospital , 55 Fruit Street, Boston 02114, United States.
³ Department of Radiology, Harvard Medical School , 55 Fruit Street, Boston 02114, United States.
⁴ Advion BioSystems, 10 Brown Road, Suite 101, Ithaca, New York 14850, United States.

PMID: 28085289
DOI: 10.1021/acs.orglett.6b03730

Abstract

In this work, we describe the ¹⁸F-labeling of α,α-difluoro-α-(aryloxy)acetic acid derivatives and demonstrate that these building blocks are amenable to post-¹⁸F-fluorination functionalization. Protodecarboxylation offers a new entry to ¹⁸F-difluoromethoxyarene, and the value of this approach is further demonstrated with coupling processes leading to representative ¹⁸F-labeled TRPV1 inhibitors and TRPV1 antagonists.

Publication types

Research Support, Non-U.S. Gov't