Triethylamine → HCID 53686009, compound

Participants

Reaction Steps

To a round bottom flask charged with 4-((tert-butoxycarbonyl)amino)butanoic acid (0.5 g, 2.46 mmol) in DCM (10 mL) was added Et3N (1.03 mL, 7.36 mmol), EDCI (706 mg, 2.46 mmol), DMAP (30 mg, 0.246 mmol) and allowed to stir overnight at RT. The reaction was quenched with water (10 mL) and extracted with DCM (2×10 mL). Combined organics washed with 10% citric acid (10 mL), brine (10 mL), dried over Na2SO4 and concentrated in vacuo. The crude material was dissolved in AcOH (7 mL) and stirred at 65° C. for 1 h. The mixture was diluted with saturated bicarbonate (15 mL) and extracted with DCM (2×15 mL), and again worked up in the above manner. The title compound was obtained as a white solid (433 mg, 64%) and used without further purification. 1H NMR (400 MHz, CDCl3) δ 7.57 (m, 2H), 7.20 (m, 2H), (4.98 (s, 2H), 3.24 (m, 2H), 2.95 (m, 2H), 1.92 (m, 2H), 1.47 (s, 9H). ESI-LRMS: [M+H]+=276 m/z.

Provenance & Evidence