Dimethylformamide → (S)-2-(4'-Cyclopropylcarbamoyl-biphenyl-3-ylcarbamoyl)-pyrrolidine-1-carboxylic acid benzyl ester
反応式
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16](=[O:33])[NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20](B2OC(C)(C)C(C)(C)O2)[CH:19]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:35]1[CH:46]=[CH:45][C:38]([C:39]([NH:41][CH:42]2[CH2:44][CH2:43]2)=[O:40])=[CH:37][CH:36]=1.CN(C=O)C>CO.C([O-])(O)=O.[Na+]>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16](=[O:33])[NH:17][C:18]1[CH:19]=[C:20]([C:35]2[CH:36]=[CH:37][C:38]([C:39](=[O:40])[NH:41][CH:42]3[CH2:44][CH2:43]3)=[CH:45][CH:46]=2)[CH:21]=[CH:22][CH:23]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1参加物
6
反応物 3
生成物 1
試薬・触媒・溶媒 2
反応条件
- 温度
- 70 °C
実験手順
A solution of (S)-2-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylcarbamoyl]-pyrrolidine-1-carboxylic acid benzyl ester (74 mg, 0.16 mmol), 4-bromo-N-cyclopropyl-benzamide (39.7 mg, 0.17 mmol), and Pd[P(Ph)3]4 (13.7 mg, 7.2 mol %) in methanol (2 mL), NaHCO3 (sat. aq., 300 μL), and DMF (400 μL) was degassed and heated to 70° C. overnight in a sealed vial. The reaction was cooled, filtered, and purified by reverse phase HPLC to give the desired product. Yield 5.3 mg. MS: 484.2 (M+H+); H1 NMR (DMSO-d6): δ (ppm) 0.51-0.70 (m, 4H), 1.76-1.98 (m, 3H), 2.08-2.30 (m, 1H), 2.77-2.86 (m, 1H), 3.38-3.52 (m, 2H), 4.27-4.37 (m, 1H), 4.86-5.08 (m, 2H), 6.96-7.65 (m, 7
後処理
- temperatureThe reaction was cooled
- filtrationfiltered
- custompurified by reverse phase HPLC
出典と根拠
- ORDレコード
- ord-e0e286ce79ba47c39297daa10c5b9eea
- 出典データセット
- uspto-grants-2009_12
- 特許番号
- US07629340B2
反応ノート
読み込み中…