Sodium Iodide → Nalpha-Boc-Ndelta-Cbz-Ornithinyl 2-Benzothiazolyl Thioether

Participants

Reaction Steps

A solution of Nα-Boc-Nδ-Cbz-ornithinol methanesulfonate (100 mg), sodium iodide (70 mg), dimethylformamide (2.5 ml), 2-mercaptobenzothiazole (70 mg) and diisopropylethylamine (85 μl) was stirred at 70° C. for 12 h. After cooling to ambient temperature, the reaction mixture was poured into ethyl acetate and worked up. The crude material was chromatographed over silica gel (20 to 50 % ethyl acetate/hexane) to afford titled product (50 mg) as a white solid: 1H NMR (400 MHz, CDCl3) δ1.39 (s, 9H), 1.58-1.69 (m, 4H), 3.22 (m, 2H), 3.54 (m, 2H), 3.99 (m, 1H), 5.12 (s, 2H), 7.23-7.42 (m, 1H), 7.77 (d, J=10.3 Hz, 1H), and 7.86 (d, J=9.7 Hz, 1H).

Provenance & Evidence