1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-BOC-4-amino-3-methoxybenzoyl methionine methyl ester

Participants

Reaction Steps

N-BOC-4-amino-3-methoxybenzoic acid (0.35 g, 1.31 mmol) was reacted with methionine methyl ester hydrochloride (0.9 g, 1.43 mmol) using EDCI as in N-BOC-4-aminobenzoyl methionine methyl ester. After recrystallization from ethyl acetate and hexanes, 0.36 g (57.2 %) of pure product was obtained. mp 163°-165° C.; 1H NMR (CDCl3) 1.53 (9 H, s), 2.09-2.18 (4 H, m), 2.23-2.35 (1 H, m), 2.60 (2 H, t, J=6.9 Hz), 3.80 (3 H, s), 3.93 (3 H, s), 4.92 (1 H, br s), 6.93 (1 H, d, J=7.6 Hz), 7.25 (1 H, m), 7.31 (1 H, d, J=10.2 Hz), 7.44(1 H, s), 8.15(1 H, d, J=8.5 Hz); 13C NMR (CDCl3) 15.47, 28.23, 30.09, 31.48, 52.06, 52.54, 55.81, 80.82, 98.06, 109.38, 116.66, 119.31, 131.52, 147.23, 152.31, 166.57, 172.58; m/ z (FAB) 413 (M+1).

Provenance & Evidence