Methanol → HCID 21967809、化合物
反応式
[C:1]([O:4][C:5]1[C:22]([C:23]([OH:25])=[O:24])=[CH:21][C:20]2[C@@H:19]3[C@H:10]([C@H:11]4[C@@:15]([CH2:17][CH2:18]3)([CH3:16])[C:14](=[O:26])[CH2:13][CH2:12]4)[CH2:9][CH2:8][C:7]=2[CH:6]=1)(=[O:3])[CH3:2].S(Cl)(Cl)=O.CO.[CH2:33](N(CC)CC)C>ClC(Cl)C.CN(C=O)C.CCOC(C)=O>[C:1]([O:4][C:5]1[C:22]([C:23]([O:25][CH3:33])=[O:24])=[CH:21][C:20]2[C@@H:19]3[C@H:10]([C@H:11]4[C@@:15]([CH2:17][CH2:18]3)([CH3:16])[C:14](=[O:26])[CH2:13][CH2:12]4)[CH2:9][CH2:8][C:7]=2[CH:6]=1)(=[O:3])[CH3:2]参加物
8
反応条件
- 温度
- 80 °C
実験手順
To a solution of 3-acetoxyestra-1,3,5(10)-trien-17-one-2-carboxylic acid (62, 1.07 g, 3.0 mmol) in dichloroethane (10 mL) was added thionyl chloride (0.28 mL, 3.9 mmol) and DMF (1 drop) at room temperature. The reaction mixture was stirred for 30 min at 80° C. After the reaction mixture was cooled to 0° C., MeOH (5.0 mL) and triethylamine (1.0 mL) were added, and stirred for 1 h. The reaction mixture was diluted with EtOAc and washed with H2O, saturated aqueous NaCl, and then dried (Na2SO4). The desiccant was filtered and the solvent was evaporated at reduced pressure. The residue was purified by column chromatography (silica gel) using n-hexane:EtOAc (3:1→3:2, v/v) to afford 0.764 g of 63 (69% yield) mp: 182-183° C.
後処理
- temperatureAfter the reaction mixture was cooled to 0° C.
- stirringstirred for 1 h
- washwashed with H2O, saturated aqueous NaCl
- dry with materialdried (Na2SO4)
- filtrationThe desiccant was filtered
- customthe solvent was evaporated at reduced pressure
- customThe residue was purified by column chromatography (silica gel)
出典と根拠
- ORDレコード
- ord-466054b820db44afa1d93f0f2fa4a987
- 出典データセット
- uspto-grants-2000_04
- 特許番号
- US06046186
反応ノート
読み込み中…