反応式
[C:1]([O:5][C:6](=[O:15])[CH2:7][C@H:8]([CH2:12][CH:13]=[CH2:14])[C:9]([OH:11])=[O:10])([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.O[CH2:21][C@H:22]([NH:29][C:30](=[O:35])[CH2:31][CH2:32][CH:33]=[CH2:34])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.CCN(C(C)C)C(C)C>CN(C=O)C.CN(C1C=CN=CC=1)C>[CH2:12]([C@@H:8]([CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:15])[C:9]([O:11][CH2:21][C@H:22]([NH:29][C:30](=[O:35])[CH2:31][CH2:32][CH:33]=[CH2:34])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:10])[CH:13]=[CH2:14]参加物
反応物 4
生成物 1
試薬・触媒・溶媒 2
実験手順
To a solution of (S)-2-(2-tert-butoxy-2-oxoethyl)pent-4-enoic acid (684 mg, 3.19 mmol) in DMF (25 mL) cooled in an ice/water bath was added EDC (612 mg, 3.19 mmol) and the resulting solution was stirred for 30 min. (R)-N-(2-hydroxy-1-phenylethyl)pent-4-enamide (700 mg, 3.19 mmol), iPr2NEt (1.77 mL, 9.58 mmol), and DMAP (39.0 mg, 0.319 mmol) were subsequently added and the reaction mixture was stirred 16 h at which point LC-MS analysis indicated the presence of both starting material and desired product. The reaction mixture was diluted with saturated NH4Cl and EtOAc and the layers separated. The aqueous layer was extracted 2× with EtOAc and the combined organic extracts were washed with 1 N HCl and brine, dried over Na2SO4, filtered, and concentrated. The crude product was purified using silica gel chromatography (MeOH/CH2Cl2 gradient) to yield 340 mg of product as a colorless oil in 26% yield. LRMS (M+Na)+: 438.4.
後処理
- additionwere subsequently added
出典と根拠
- ORDレコード
- ord-d71ae031ebc240d5ad4a4f7bf7f8a38e
- 出典データセット
- uspto-grants-2013_09
- 特許番号
- US08530456B2
関連ノート
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