1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 18682345, compound

Participants

Reaction Steps

To a stirred solution of 4-methyl-2-{2-[4-(3-o-tolyl-ureido)-phenyl]-acetylamino}-pentanoic acid (3.6 g), 4-amino-3-hydroxy-butyric acid benzyl ester hydrochloride (1.6 g), triethylamine (1 ml) and HOBT (1.06 g) in DMF (50 ml) at room temperature was added EDCI (1.63 g). After stirring 16 h the mixture was poured into 1500 ml ice-water and stirred for 20 min. The resulting ppt was filtered and dried to give a creme colored solid. Recrystallization from EtOAc gave 2.1 g of the title compound as a white solid. MS [M+1]+589.2; 1H nmr (400 MHz, DMSO-d6) δ0.73-0.81 (m, 6H), 1.37-1.49 (m, 3H), 2.19 (s, 3H), 2.20-2.28 (m, 1H), 2.46-2.49 (m, 1H), 2.99-3.09 (m, 2H), 3.33 (q, J=13.8 Hz, 2H), 3.90 (m, 1H), 4.19-4.23 (m, 1H), 5.05 (s, 2H), 6.88 (t, 1H), 7.06-7.12 (m, 4H), 7.26-7.34 (m, 6H), 7.75 (d, J=8.1 Hz, 1H), 7.92 (dt, 1H), 8.06 (s, 1H), 8.10 (d, J=8.1 Hz, 1H), 9.13 (s, 1H).

Provenance & Evidence