反应详情

Solution of Nα-Boc-Nδ-Cbz-ornithinol (587 mg), dichloromethane (17 ml), 2-naphthol (288 mg), triphenylphosphine (524 mg) and N,N′-diisopropylazodicarboxamide (393 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 (534 mg) as a glassy solid: 1H NMR (400 MHz, CDCl3) δ1.41 (s, 9H), 1.60-1.73 (m, 4H), 3.20 (m, 2H), 4.01 (m, 3H), 5.07 (s, 2H), 7.09 (s, 1H), 7.11 (d, J=8.3 Hz, 1H), 7.28 (m, 6H), 7.40 (t, J=8.4 Hz, 1H), and 7.71 (m, 3H).

1. washwashed successively with saturated sodium bicarbonate and brine
2. dry with materialThe organic phase was then dried over anhydrous sodium sulfate
3. concentrationconcentrated in vacuo
4. customFurther purification by flash chromatography