反応式
[C:1]([C:4]1[N:5]=[C:6]([NH:9][C:10](=[O:33])[C@@H:11]([NH:20][C:21](=[O:32])[C@H:22]([NH2:31])[C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[C@H:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH3:13])[S:7][CH:8]=1)(=[O:3])[CH3:2].C(N(C(C)C)CC)(C)C.[O:43]=[C:44](Cl)OC(Cl)(Cl)Cl>O1CCCC1.C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:1]([C:4]1[N:5]=[C:6]([NH:9][C:10](=[O:33])[C@@H:11]([N:20]2[C:21](=[O:32])[C@@H:22]([C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=3)[NH:31][C:44]2=[O:43])[C@H:12]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH3:13])[S:7][CH:8]=1)(=[O:3])[CH3:2]参加物
反応物 3
生成物 1
試薬・触媒・溶媒 3
反応条件
- 温度
- 0 °C
実験手順
(2S,3S)-N-(4-Acetyl-thiazol-2-yl)-2-[(R)-2-amino-2-(4-methoxy-phenyl)-acetylamino]-3-phenyl-butyramide (2.7 g, 90% purity, 5.2 mmol) and diisopropylethylamine (4.2 mL, 23.6 mmol) in tetrahydrofuran (50 mL) were added to a solution of diphosgene (0.48 mL, 4 mmol) in a mixture of toluene (50 mL) and tetrahydrofuran (50 mL) over 10 minutes at 0° C. The mixture was stirred at 0° C. for 20 minutes and diluted with ethyl acetate. The mixture was washed with water, brine and dried (sodium sulfate). Evaporation of the solvents and chromatography of the residue over silica gel with 0.4-1% v/v methanol in dichloromethane gave (2S,3S)-N-(4-acetyl-thiazol-2-yl)-2-[(R)-4-(4-methoxy-phenyl)-2,5-dioxo-imidazolidin-1-yl]-3-phenyl-butyramide (2.36 g, 92%) as a white solid.
後処理
- washThe mixture was washed with water, brine
- dry with materialdried (sodium sulfate)
- customEvaporation of the solvents and chromatography of the residue over silica gel with 0.4-1% v/v methanol in dichloromethane
出典と根拠
- ORDレコード
- ord-269506ebc9e54b1dac5e31a8e9d82d6e
- 出典データセット
- uspto-grants-2008_09
- 特許番号
- US07427635B2
関連ノート
読み込み中…