Benzyl chloroformate → 11-(((Benzyloxy)carbonyl)amino)undecanoic acid

Participants

Reaction Steps

To a suspension of 11-aminoundecanoic acid (17) in 1:1 water/dioxane (160 mL total) was added K2CO3 (10.28 g, 74.51 mmol) followed by the slow addition over 30 min of benzylchloroformate (CbzCl, 4.55 mL, 32.29 mmol), and the mixture was stirred at room temperature for 2 h. The solid was then removed by filtration, washed with water (3×30 mL) and dried in a vacuum oven at 40° C. for 72 h to afford a white solid 18 (2.91 g, 35% yield): 1H NMR (500 MHz, CD3OD) δ 1.36 (m, 12H), 1.50 (m, 2H), 1.62 (m, 2H), 2.18 (m, 2H), 3.08 (m, 2H), 5.14 (s, 2H), 7.38 (m, 5H); m/z (ESI) 336 [M+H]+.

Provenance & Evidence