1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Methyl-2-{2-[4-(3-o-tolyl-ureido)-phenyl]-acetylamino}-pentanoic acid benzyl ester

Participants

Reaction Steps

To a stirred solution of [4-(3-o-tolyl-ureido)-phenyl]-acetic acid (3.0 g), L-leucine benzyl ester (4.2 g), triethylamine (1.6 ml), and HOBT (1.6 g) in dry DMF (50 ml) at room temperature was added EDCI (2.4 g). After 16 h the mixture was poured into water (400 ml) and extracted with EtOAc (400 ml×2). The combined organics were washed with 5% citric acid (100 ml); saturated NaHCO3 (100 ml); water (100 ml), brine (100 ml); dried over MgSO4; filtered, and concentrated under reduced pressure to about 100 ml. The resulting suspension was filtered to give 4.0 g of the title compound as a white solid. MS [M+1]+488.2; 1H nmr (400 MHz, DMSO-d6) δ0.79 (d, J=6.4 Hz, 3H), 0.86 (d, J=6.4 Hz, 3H), 1.45-1.63 (m, 3H), 2.21 (s, 3H), 3.37 (s, 2H), 4.26-4.31 (m, 1H), 5.07 (s, 2H), 6.91 (t, 1H), 7.09-7.15 (m, 4H), 7.29-7.37 (m, 7H), 7.81 (d, 1H), 7.86 (s, 1H), 8.44 (d, 1H), 8.93 (s, 1H).

Provenance & Evidence