Allylamine → HCID 131718648, compound

Participants

Reaction Steps

Under a nitrogen atmosphere, Cbz-Phe-OH (1.00 g, 3.35 mmol) was dissolved in 10 mL of anhydrous methylene chloride containing 1-hydroxybenzotriazole monohydrate (0.57 g, 3.69 mmol) and 1-(3-dimethylaminopropyl)-ethylcarbodiimide hydrochloride (0.71 g, 3.69 mmol) and stirred at ice bath temperature for 1.5 hour. Allylamine (0.19 g, 3.35 mmol) was added and the solution was stirred at 0° C. for 5 hours and then allowed to warm to ambient temperature overnight. The solvent was evaporated, and the residue was dissolved in ethyl acetate and washed with saturated aqueous KHSO4, water, saturated aqueous sodium bicarbonate, water, and brine, prior to drying and evaporation. Recrystallization from ethyl acetate/hexane afforded 0.56 g (50% yield) of the title compound as a white solid product; 1H NMR (CDCl3) δ3.03 (dd, J=15 and 7.5 Hz, 1H), 3.14 (dd, J=15 and 7.5 Hz, 1H), 3.76-3.82 (m, 2H), 4.33-4.42 (m, 1H), 4.96-5.08 (m, 2H), 5.10 (s, 2H), 5.33 (br s, 1H), 5.59-5.74 (m, 2H), 7.15-7.40 (m, 10H). MS (DCI) m/e 356 (M+NH4)+, 339 (M+H)+.

Provenance & Evidence