反応式
[Cl-].[Li+].[CH:3]([O:6][C:7]([N:9]1[CH:14]([CH2:15][CH3:16])[CH:13](C(OCC)=O)[C:12](=[O:22])[C:11]2[S:23][CH:24]=[CH:25][C:10]1=2)=[O:8])([CH3:5])[CH3:4]>CS(C)=O.O>[CH:3]([O:6][C:7]([N:9]1[CH:14]([CH2:15][CH3:16])[CH2:13][C:12](=[O:22])[C:11]2[S:23][CH:24]=[CH:25][C:10]1=2)=[O:8])([CH3:4])[CH3:5]参加物
反応物 2
生成物 1
試薬・触媒・溶媒 2
反応条件
- 温度
- 160 °C
実験手順
Add lithium chloride (0.162 g, 3.83 mmol) in one portion to a mixture of 5-ethyl-7-oxo-6,7-dihydro-5H-thieno[3,2-b]pyridine-4,6-dicarboxylic acid 6-ethyl ester 4-isopropyl ester (0.520 g, 1.53 mmol) in dimethylsulfoxide (15 ml) and water (2 drops). Heat the mixture at 160° C. for 4 h. Cool the reaction to room temperature and partition between ethyl acetate (50 ml) and brine (50 ml). Separate the organic layer and wash with brine (3×50 ml). Dry the organic portion over sodium sulfate, filter and concentrate. Purify using silica gel column chromatography (gradient eluent, 0-15% ethyl acetate in hexane) to give 5-ethyl-7-oxo-6,7-dihydro-5H-thieno[3,2-b]pyridine-4-carboxylic acid isopropyl ester (0.236 g, 58% for two steps) as an oil. MS (ES+): 268 (M+H).
後処理
- temperatureCool
- customthe reaction to room temperature
- custompartition between ethyl acetate (50 ml) and brine (50 ml)
- customSeparate the organic layer
- washwash with brine (3×50 ml)
- dry with materialDry the organic portion over sodium sulfate
- filtrationfilter
- concentrationconcentrate
- customPurify
出典と根拠
- ORDレコード
- ord-1d5f050819e34f279e96e73b66336a50
- 出典データセット
- uspto-grants-2008_12
- 特許番号
- US07470705B2
関連ノート
読み込み中…