5-[1-(3-Phenyl-allyl)-1H-indol-3-yl]-4-(7-phenyl-heptanoylamino)-pent-2-enoic acid methyl ester → (S)-4-(7-Phenyl-heptanoylamino)-5-[1-(3-phenyl-propyl)-1H-indol-3-yl]-pentanoic acid methyl ester
反応式
[CH3:1][O:2][C:3](=[O:41])[CH:4]=[CH:5][CH:6]([NH:26][C:27](=[O:40])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([CH2:17][CH:18]=[CH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:9]=1>CO.[Pd]>[CH3:1][O:2][C:3](=[O:41])[CH2:4][CH2:5][C@H:6]([NH:26][C:27](=[O:40])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([CH2:17][CH2:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:9]=1参加物
4
実験手順
5-[1-(3-Phenyl-allyl)-1H-indol-3-yl]-4-(7-phenyl-heptanoylamino)-pent-2-enoic acid methyl ester (118 mg, 0.215 mmol) in MeOH (60 mL) was hydrogenated at 15 psi for 15 minutes using 10% Pd/C. The solution was filtered and the solvent removed to afford the title compound (111 mg, 93%). ESMS 553 (M+H+), mp 79.4-81° C. 1H NMR (CDCl3) δ 7.62 (1H, d, J=7.74 Hz). 7.31-7.07 (13H, m), 6.93 (1H, s), 5.43 (1H, d, J=8.37 Hz), 4.32-4.22 (1H, m), 4.08 (2H, t, J=6.96 Hz), 3.62 (3H, s), 2.97 (1H, dd, J=5.37, 14.43 Hz), 2.91 (1H, dd, J=6.54, 14.43 Hz), 2.62 (2H, t, J=7.62 Hz), 2.57 (2 h, t, J=7.73 Hz), 2.41-2.10 (4H, m), 2.06 (2H, t, J=7.62 Hz), 1.97-1.26 (10H, m). 13C NMR (CDCl3) δ 174.3, 172.9, 142.7, 140.9, 136.2, 132.1, 128.5, 128.4, 128.3, 128.2, 126.4, 126.1, 125.6, 121.6, 119.1, 119.0, 110.2, 109.4, 51.6, 49.5, 45.5, 36.9, 35.8, 32.9, 31.5, 31.2, 31.0, 30.6, 29.1, 28.9, 25.6. ISMS: 553 (M+H).