Triethylamine → HCID 58996981, compound

Participants

Reaction Steps

To a solution of COMPOUND 249 (0.1054 g, 0.34 mmol) in MeOH (4 mL) was added Et3N (0.1 mL, 0.68 mmol) and ethyl acetimidate hydrochloride (0.0549 g, 0.41 mmol), and stirred at room temperature for 24 hours then concentrated. Saturated NaHCO3 (15 mL) was added and extracted with CH2Cl2 (2×40 mL). Purification of the crude material by column chromatography on silica gel (15:1:1 CH2Cl2-MeOH—NH4OH) followed by radial chromatography on silica gel (50:3:2 CH2Cl2-MeOH—NH4OH) provided 0.0408 g (34%) of COMPOUND 338 as a white solid. 1H NMR (CDCl3) δ 1.60-1.72 (m, 2H), 1.90-1.95 (m, 2H), 2.09 (s, 6H), 2.12 (s, 3H), 2.47-2.68 (m, 4H), 3.82 (s, 4H), 4.17 (d, 2H, J=12.3 Hz), 7.06-7.10 (m, 2H), 7.37 (d, 2H, J=7.2 Hz), 8.34 (d, 2H, J=4.5 Hz). 13C NMR (CDCl3) δ 18.39, 23.92, 27.33, 45.64, 55.06, 57.89, 122.77, 133.81, 138.40, 146.29, 157.63, 164.64. ES-MS m/z 352.5 (M+H).

Provenance & Evidence