Ethane, 2-bromo-1,1-diethoxy- → ethyl((1S)-5-{3-[2-methoxy-4-(1,3-thiazol-2-yl)phenoxy]propoxy}-2,3-dihydro-1h-inden-1-yl)acetate

HRID 603427ノート

反応式

HRID 603427 の反応式
[NH2:1][C:2]([C:4]1[CH:29]=[CH:28][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[C@H:18]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:17][CH2:16]3)=[C:6]([O:30][CH3:31])[CH:5]=1)=[S:3].[CH2:32](OC(OCC)CBr)[CH3:33]>CCO.O>[CH2:26]([O:25][C:23](=[O:24])[CH2:22][C@H:18]1[C:19]2[C:15](=[CH:14][C:13]([O:12][CH2:11][CH2:10][CH2:9][O:8][C:7]3[CH:28]=[CH:29][C:4]([C:2]4[S:3][CH:32]=[CH:33][N:1]=4)=[CH:5][C:6]=3[O:30][CH3:31])=[CH:21][CH:20]=2)[CH2:16][CH2:17]1)[CH3:27]

参加物

5

反応物 2

HCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 16110447ethyl ((1S)-5-{3-[4-(aminocarbonothioyl)-2-methoxyphenoxy]propoxy)-2,3-dihydro-1H-inden-1-yl)acetate

生成物 1

HCID 16110449ethyl((1S)-5-{3-[2-methoxy-4-(1,3-thiazol-2-yl)phenoxy]propoxy}-2,3-dihydro-1h-inden-1-yl)acetate収率 58%

試薬・触媒・溶媒 2

HCID 962Water触媒HCID 702Ethanol溶媒

反応条件

温度
70 °C

実験手順

Ethyl ((1S)-5-{3-[4-(aminocarbonothioyl)-2-methoxyphenoxy]propoxy}-2,3-dihydro-1H-inden-1-yl)acetate (1.00 g, 2.3 mmol) (Example 146) and bromoacetaldehyde diethyl acetal (1.78 g, 9.2 mmol) were dissolved in EtOH (30 mL) and water (2 drops) was added. The mixture was heated at 70° C. for 18 h, and then the reaction mixture was cooled to rt, and concentrated under reduced pressure. Purification by silica gel flash chromatography (EtOAc:hexane (v/v)=1:1) gave 610 mg (58%) of the title compound as a clear oil. LC-MS: RT=3.81 min; (M+H)+ 468.1.

後処理

  1. temperaturethe reaction mixture was cooled to rt
  2. concentrationconcentrated under reduced pressure
  3. customPurification by silica gel flash chromatography (EtOAc:hexane (v/v)=1:1)

出典と根拠

ORDレコード
ord-a96ee81f5d16439b826fbbf00885b2c5
出典データセット
uspto-grants-2011_03
特許番号
US07906653B2

反応ノート

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