Boc-Phenylalanyl-Ndelta-Cbz-ornithinyl 2-Naphthyl Thioether → Phenylalanyl-Ornithinyl 2-Naphthyl Thioether Trifluoroacetate

Participants

Reaction Conditions

Reaction Steps

A solution of Boc-phenylalanyl-Nδ-Cbz-ornithinyl 2-naphthyl thioether (C) (30 mg) and a mixture of trifluoroacetic acid-triethylsilane (3:1) (10 ml) was stirred at 25° C. for 1 hr and concentrated in vacuo. The crude material was purified by HPLC to afford desired product (10 mg) as a white solid: HPLC (method A, retention time=46.26 min); 1H NMR (400 MHz, D2O) δ1.69 (m, 2H), 1.77 (m, 1H), 1.87 (m, 1H), 2.84 (t, J=8.4, 2H), 3.02 (m, 2H), 3.09 (dd, J=14.4; 7.2 Hz, 1H), 3.22 (dd, J=14.0 5.2 Hz, 1H), 4.15 (t, J=8.0 Hz, 1H), 7.16 (m, 2H), 7.34 (m, 3H), 7.48 (m, 1H), 7.60 (m, 3H), 7.93 (t, J=7.2, 1H), and 7.97 (m, 2H).

Provenance & Evidence