[Cl:1][C:2]1[CH:3]=[C:4]([C@@:8]([C@@H:17]2[CH2:22][CH2:21][CH2:20][NH:19][CH2:18]2)([O:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH3:9])[CH:5]=[CH:6][CH:7]=1.[CH:23]1([CH2:29][C@H:30]([NH:43][C:44](=O)[O:45]C2C=CC([N+]([O-])=O)=CC=2)[CH2:31][N:32]([CH3:42])[C:33]([O:35][CH2:36][CH2:37][Si:38]([CH3:41])([CH3:40])[CH3:39])=[O:34])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C@@:8]([C@@H:17]2[CH2:22][CH2:21][CH2:20][N:19]([C:44](=[O:45])[NH:43][C@H:30]([CH2:31][N:32]([CH3:42])[C:33]([O:35][CH2:36][CH2:37][Si:38]([CH3:41])([CH3:40])[CH3:39])=[O:34])[CH2:29][CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[CH2:18]2)([O:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH3:9])[CH:5]=[CH:6][CH:7]=1A mixture of ethyl 2-((R)-1-(3-chlorophenyl)-1-((R)-piperidin-3-yl)ethoxy)acetate, (S)-4-nitrophenyl 1-cyclohexyl-3-(methyl((2-(trimethylsilyl)ethoxy)carbonyl)amino)propan-2-ylcarbamate (0.096 g, 0.20 mmol), and DIPEA (1 mL) in CH2Cl2 was stirred at rt for 24 h. After the reaction mixture was evaporated under reduced pressure, the crude product was purified by reversed-phase HPLC to afford 0.0425 g (47% in two steps) of ethyl 2-((R)-1-(3-chlorophenyl)-1-((R)-1-((S)-1-cyclohexyl-3-(methyl((2-(trimethylsilyl)ethoxy)carbonyl)amino)propan-2-ylcarbamoyl)piperidin-3-yl)ethoxy)acetate. MS ESI +ve m/z 668 (M+H).
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