1-Hydroxybenzotriazole → HCID 86757773, compound

Participants

Reaction Steps

HOBT (255 mg) was added to a solution of N-(t-butoxycarbonyl)leucine (297 mg) in DMF (5 ml), followed by 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (273 mg) and the solution stirred for 15 min. Methyl 3-amino-5-hexenoate hydrochloride (185 mg) was dissolved in DMF (5 ml) and triethylamine (140 μl) and the resultant solution added to the solution of the N-(t-butoxycarbonyl)leucine activated ester followed by diisopropylethylamine (100 μl). The mixture was stirred overnight at ambient temperature. The mixture was added to ethyl acetate(30 ml), washed with water (2×5 ml), 5% citric acid (3 ml), water (5 ml), saturated sodium bicarbonate solution (5 ml), water (5 ml), saturated brine (5 ml), dried (MgSO4) and evaporated to give methyl N-(t-butoxycarbonyl)leucine-3-amino-5-hexenoate (335 mg); NMR (CDCl3): 0.9 (6H, d), 1.4(10H, m), 1.6-1.8 (2H, m), 2.2-2.3 (2H,m), 2.5(2H,d), 3.6(3H,s), 4.0-4.1(1H, m), 4.2-4.3 (1H,m), 4.8-4.9(1H,b), 5.0-5.1 (2H,d), 5.6-5.8 (1H,m), 6.5-6.6(1H,m): m/Z 357 (M+H)

Provenance & Evidence