4-Ethoxycarbonyl-1-(1-(benzyloxycarbonyl)amino-3-(1,1-dimethylethoxycarbonyl)propyl)carbonylpiperazine → 4-Ethoxycarbonyl-1-(1-amino-3-(1,1-dimethylethoxycarbonyl)propyl)carbonylpiperazine
反応式
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12]([CH:14]([NH:24]C(OCC2C=CC=CC=2)=O)[CH2:15][CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[O:13])[CH2:8][CH2:7]1)=[O:5])[CH3:2]>CO.[Pd]>[CH2:1]([O:3][C:4]([N:6]1[CH2:7][CH2:8][N:9]([C:12]([CH:14]([NH2:24])[CH2:15][CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[O:13])[CH2:10][CH2:11]1)=[O:5])[CH3:2]参加物
実験手順
Alternatively, N-benzyloxycarbonyl-L-glutamic acid y-t-butyl ester (34 g, 100 mmol) and EDCI (22 g, 110 mmol), HOBT (15 g, 110 mmol) were combined in 800 mL CH2Cl2 with triethylamine (24 mL, 172 mmol). The resulting reaction mixture was stirred at ambient temperature for 20 minutes, then 1-ethoxycarbonylpiperazine (18 g, 120 mmol) was added. The resulting mixture was stirred at ambient temperature for 15 hours. The reaction mixture was then washed with water, 2N NaHSO4, and brine, then concentrated in vacuo to afford an oil, which was purified by flash column chromatography on silica gel (acetate/hexane=1/1) to afford 4-ethoxycarbonyl-1-(1-(benzyloxycarbonyl)amino-3-(1,1-dimethylethoxycarbonyl)propyl)carbonylpiperazine (40 g). 4-ethoxycarbonyl-1-(1-(benzyloxycarbonyl)amino-3-(1,1-dimethylethoxycarbonyl)propyl)carbonylpiperazine (40 g) was dissolved in 200 mL of MeOH, 2 g Pd/C(10%) was added and hydrogenated at 50 psi for 1 hour. Regular work up afforded 4-ethoxycarbonyl-1-(1-amino-3-(1,1-dimethylethoxycarbonyl)propyl)carbonylpiperazine (25 g).
出典と根拠
- ORDレコード
- ord-4e344923b8de4e4cb0fa455e94767689
- 出典データセット
- uspto-grants-2006_08
- 特許番号
- US07084142B2
反応ノート
読み込み中…