Hydrochloric Acid → methyl N-[(4'-amino-3-methylbiphenyl-4-yl)carbonyl]-L-valinate

반응식

[CH3:1][C:2]1[CH:3]=[C:4]([C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][CH:20]=2)[CH:5]=[CH:6][C:7]=1[C:8]([NH:10][C@H:11]([C:15]([O:17][CH3:18])=[O:16])[CH:12]([CH3:14])[CH3:13])=[O:9].Cl>C(O)C.[Fe]>[NH2:25][C:22]1[CH:21]=[CH:20][C:19]([C:4]2[CH:5]=[CH:6][C:7]([C:8]([NH:10][C@H:11]([C:15]([O:17][CH3:18])=[O:16])[CH:12]([CH3:14])[CH3:13])=[O:9])=[C:2]([CH3:1])[CH:3]=2)=[CH:24][CH:23]=1

참가 물질

실험 절차

Iron powder (0.79 g, 14 mmol) was added to a solution of methyl N-[(3-methyl-4′-nitrobiphenyl-4-yl)carbonyl]-L-valinate (0.65 g, 1.4 mmol) in ethanol (20 mL). Concentrated HCl (0.71 mL, 1.4 mmol) was added, and the mixture was heated at reflux for 1 h. Upon cooling to rt, the mixture was filtered through a pad of Celite®, and the filtrate was concentrated in vacuo. The material was purified by column chromatography (33% EtOAc in hexanes), yielding 0.50 g (quantitative) of the title compound. LC/MS m/z 341.1 (MH+), retention time 2.19 min. 1H NMR (400 MHz, CD2Cl2) δ 1.06 (dd, 6H), 2.32-2.39 (m, 1H), 2.50 (s, 3H), 3.78 (s, 3H), 4.71-4.78 (m, 1H), 6.33 (d, 1H), 6.78 (d, 2H), 7.38-7.44 (m, 5H).