2-Naphthol → Nalpha-Benzyl-Ndelta-Boc-Nalpha-Methylornithinyl 2-Naphthyl Ether

Participants

Reaction Steps

A μιξτυρε Oφ Nα-benzyl-Nδ-Boc-Nα-methylornithinol (168 mg), dichloromethane (10 ml), 2-naphthol (91 mg), triphenylphosphine (165 mg), and N,N′-diisopropylazodicarboxamide (124 μl) was stirred for 12 hrs at 25° C., under nitrogen. The reaction mixture was poured into dichloromethane and washed successively with saturated sodium bicarbonate and brine. The organic phase was then dried over anhydrous sodium sulfate and concentrated in vacuo. Further purification by flash chromatography gave the titled product (90 mg) as a white solid. 1H NMR (400 MHz, CDCl3) δ1.51 (s, 9H), 1.68 (m, 2H), 1.75 (m, 2H), 2.39 (s, 3H), 3.20 (m, 2H), 3.82 (d, J=13.3, 1H), 3.93 (d, J=13.2, 1H), 4.11 (dd, J=9.6; 3.6, 1H), 4.29 (dd, J=10.2; 8.4, 1H), 7.22 (m, 2H), 7.29 (t, J=7.8, 1H), 7.39 (m, 5H), 7.50 (t, J=8.0, 1H), 7.79 (m, 3H).

Provenance & Evidence