Molecule of the month - TetraBoc-L-DOPA methyl ester

Welcome to our next molecule of the month 2024 - TetraBoc-L-DOPA methyl ester
Copper-mediated 18F-radiofluorination has been extended to the use of arylstannanes as precursors [1]. This method can be used for the 18F-radiosynthesis of [18F]F-L-DOPA under mild conditions and represents a valuable alternative to the technically sophisticated and low-yielding electrophilic approach. Automated 18F-radiofluorination of the TetraBoc protected trimethyltin precusor for clinical use was performed with a radiochemical purity of >99% and a molar activity of up to 60 GBq/µmol [2].

[1] Makaravage K. J. et al. Copper-Mediated Radiofluorination of Arylstannanes with [18F]KF. Org. Lett. 2016, 18, 5440-5443; Zarad F. A Practical Method for the Preparation of 18F-Labeled Aromatic Amino Acids from Nucleophilic [18F]Fluoride and Stannyl Precursors for Electrophilic Radiohalogenation. Molecules 2017, 22, 2231.
[2] Kniess T. et al. Cu-mediated 18F-radioflourination of various stannylated FDOPA precursors - what is feasible? Poster iSRS 2023, Honolulu, Hawaii.

You can find the products here: 

1345 - TetraBoc-L-DOPA methyl ester
1310 - 6-Fluoro-L-DOPA hydrochloride