Succinamide → Butanedioic acid, 1,4-di-2-propen-1-yl ester

Participants

Reaction Steps

To a solution of 10 (380 mg, 1.1 mmol), DIPEA (1 mL, 5.7 mmol), and 11 (0.37 g, 1.2 mmol) in DMF (30 mL) was added HATU (0.43 g, 1.1 mmol) and the solution was allowed to stir for 24 h at room temperature. The solution was diluted with EtOAc (150 mL) and washed with 5% aqueous solution of LiCl (3×100 mL), 1 N HCl (1×100 mL), saturated aqueous NaHCO3 (2×100 mL), brine, dried over anhydrous Na2SO4, filtered, and concentrated to yield an pale yellow oil. This residue was further purified by column chromatography (silica gel, 3:1 Hexanes/EtOAc) to yield 12 (0.31 g, 44%) as a white foam: 1H NMR (300 MHz, CDCl3) δ 7.86-6.91 (m, 9 H), 5.82 (m, 2 H), 5.67 (m, 1 H), 5.09 (m, 4 H), 3.48 (s, 3 H), 2.73-2.28 (m, 5 H), 1.92 (m, 1 H), 1.61 (m, 1 H), 1.42 (s, 9 H), 1.27 (m, 1 H), 0.93 (m, 6 H); ESI MS m/z=626 [C35H42F3N3O4+H]+.

Provenance & Evidence