Tetrahydrofuran → Methyl N-{[(1-tert-butoxycarbonylpiperidin-4-yl)amino]carbonyl}valinate
반응식
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.C(N(CC)CC)C.Cl.[CH3:23][O:24][C:25](=[O:31])[CH:26]([CH:28]([CH3:30])[CH3:29])[NH2:27].[O:32]1CCC[CH2:33]1>>[C:11]([O:10][C:8]([N:5]1[CH2:4][CH2:3][CH:2]([NH:1][C:33]([NH:27][C@H:26]([C:25]([O:24][CH3:23])=[O:31])[CH:28]([CH3:30])[CH3:29])=[O:32])[CH2:7][CH2:6]1)=[O:9])([CH3:14])([CH3:13])[CH3:12]참가 물질
5
실험 절차
4-Amino-1-boc-piperidine (205 mg, 1.02 mmol) and triethylamine (0.143 μL, 1.02 mmol) in tetrahydrofuran (5 mL) were added to a solution of p-nitrophenylchloroformate (206 mg, 1.02 mmol) in tetrahydrofuran (15 mL) at 0° C. After 1 h, additional triethylamine was added (0.286 mL, 2.04 mmol) along with DL-valine methyl ester hydrochloride (134 mg, 1.02 mmol). The reaction warmed to ambient temperature and was then heated to 50° C. After 2 h, the mixture was filtered, concentrated and redissolved in ethyl acetate. The ethyl acetate layer was washed with 1N sodium hydroxide (3×), saturated sodium bicarbonate solution, water, brine, and dried over sodium sulfate. Purification by silica gel chromatography (100% dichloromethane→7% methanol {1% ammonium hydroxide}/dichloromethane) gave the title compound (300 mg). MS 358.28 (M+1)