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. 2023 Aug 30;66(17):12324–12341. doi: 10.1021/acs.jmedchem.3c00845

Scheme 1. Synthesis of Enamide and Acrylate Model Systems.

Scheme 1

Reagents and conditions: (i) HATU or dicyclohexylcarbodiimide (DCC), 4-dimethylaminopyridine (DMAP), N,N-dimethylformamide (DMF), 0 °C—rt, 18 h; (ii) 5FU, DABCO (cat.), DMF, rt—40 °C, 1–24 h; (iii) DABCO, DMF, 0 °C, 1.5 h; (iv) 2 M NaOH (aq), tetrahydrofuran (THF), rt, 30 min; (v) 4-nitrophenol, DCC, DMAP, DMF, 5 h, rt; (vi) 1-(2-(2-methoxyethoxy)ethoxy)-4-tosylate, K2CO3, DMF, 80 °C, 3 h; (vii) H2, Pd/C (10% wt), MeOH/dichloromethane (DCM), 40 °C 21 h; (viii) propiolic acid, HATU, DMAP, DMF, 0 °C—rt, 18 h; (ix) 5FU, DABCO, DMF, 40 °C, 40 h; (x) bis(trimethylsilyl)ethylene, AlCl3, DCM, 0 °C—rt, 18 h; (xi) tetra-n-butylammonium fluoride (TBAF), MeOH, −78 °C, 1 h; (xii) 5FU, DABCO, DMF, 40 °C, 30 min.