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. Author manuscript; available in PMC: 2020 Jun 5.
Published in final edited form as: ChemMedChem. 2019 Apr 10;14(11):1096–1107. doi: 10.1002/cmdc.201900114

Scheme 5.

Scheme 5.

Synthesis of PRP 12. Reagents and conditions: a) perfluorobenzylbromide, NaH, DMF, 14 h; b) N-methylpropargylamine, STAB-H, DCE, 5 h; c) LiOH, 6:3:1 THF/H2O/dioxane, 12 h; d) 19, EDC•HCl, HOBt, DMAP, Et3N, CHCl3, 6 h; e) NaN3, Bu4NN3, DMF, 50 °C, 22 h; f) MgBr2, DCM, 3 h. PFB: perfluorobenzyl.