1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4-Nitro-2-(3,5-dimethylphenyl)benzoyl methionine methyl ester

Participants

Reaction Steps

4-nitro-2-(3,5-dimethylphenyl)benzoic acid (0.15 g, 0.55 mmol), methionine methyl ester hydrochloride salt (0.11 g, 0.55 mmol), EDCI (0.11 g, 0.55 mmol), HOBT (0.07 g, 0.55 mmol) and Et3N (0.08 ml) in dry CH2 Cl2 (2.2 ml) were reacted and worked up according to the procedure for N-BOC-4-aminobenzoyl methionine methyl ester in Example 1. After recrystallization from ethyl acetate and hexanes, 0.13 g (58.4%) of pure product was isolated. mp 122-124° C.; 1H NMR (CDCl3) 1.2-1.84 (1 H, m), 1.85-1.97 (1 H, m), 2.01 (3 H, s), 2.05 (3 H, t, J=7.7 Hz), 2.38 (6 H, s), 3.70 (3 H, s), 4.67-4.74 (1 H, m), 6.03 (1 H, d, J=7.9 Hz), 7.05 (2 H, s), 7.09 (1 H, s), 7.84-7.87 (1 H, m), 7.84-7.87 (1 H, m), 8.23-8.26 (2 H, m); 13C NMR (CDCl3), 15.20, 21.26, 29.22, 31.15, 51.79, 52.57, 122.07, 25.11, 126.27, 130.03, 130.53, 137.77, 138.82, 140.29, 141.56, 148.41, 167.14, 171.53.

Provenance & Evidence