Hydrochloric Acid → HCID 66621435, compound

Participants

Reaction Steps

Methyl 4-(2-(benzyloxycarbonylamino)ethyl)benzoate ((3.2 g, 10.2 mmol) was added to tetrahydrofuran (34 mL) and reacted with methyl iodide (3.8 mL, 61.2 mmol), then sodium hydride (2.0 g, 51 mmol) was added batch-wise and the reaction mixture was stirred for 3 h at room temperature, and then water (1 mL) was added. The mixture was stirred at room temperature for 1 h, adjusted to pH=3 with 1N hydrochloric acid and the mixture was extracted by ethyl acetate (50 mL×3), washed by water and evaporated the solvent. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate 10:1 to 2:1, acetic acid was added) to obtain 4-(2-((benzyloxycarbonyl)(methyl)amino)ethyl)benzoic acid (2.3 g, yield 72%) as yellow oil. 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 2.79-2.85 (m, 5H), 3.49 (m, 2H), 4.95-5.04 (t, J=19 Hz, 2H), 7.24-7.37 (m, 7H), 7.83-7.86 (m, 2H), 12.8 (s, 1H); LC-MS (ESI) m/z: 314 (M+1)+.

Provenance & Evidence