反応 #48240

反応方程式

benzyl (E,4S)-4-[(2-hydroxydodecanoyl)amino]oct-2-enoate

N2

→

(4S)-4-[(2-Hydroxydodecanoyl)amino]octanoic acid

溶媒

EtOH

反応条件

後処理

1. 1
   その他The catalyst was removed by filtration through a pad of Celite
2. 2
   その他the filtrate was evaporated under reduced pressure
3. 3
   その他The product was purified by column chromatography (CHCl3/MeOH 9/1)

実験手順

To a solution of benzyl (E,4S)-4-[(2-hydroxydodecanoyl)amino]oct-2-enoate (0.445 g, 1 mmol) in EtOH (2.5 mL), through which N2 had been passed for 5 min, 10% Pd/C catalyst (0.042 g) was added. The reaction mixture was stirred under H2 for 5 h at room temperature. The catalyst was removed by filtration through a pad of Celite and the filtrate was evaporated under reduced pressure. The product was purified by column chromatography (CHCl3/MeOH 9/1). Yield 0.28 g (70%); mp 53-55° C.; [α]D−2.4 (c 0.75 CHCl3); 1H NMR δ 6.82 (1H, m, NH), 4.18 (1H, m, CHNH), 3.91 (1H, m, CHOH), 2.39 (2H, t, J=6.3 Hz, CH2COOH), 1.95-1.12 (26H, m, 13×CH2), 0.88 (3H, t, J=6.0 Hz, CH3); Anal. Calcd. for C20H39NO4: C, 67.19; H, 10.99; N, 3.92. Found: C, 67.05; H, 11.18; N, 3.63.

出典