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 603427노트

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HRID 603427 반응식
[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]

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 962Water촉매HCID 702Ethanol용매

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온도
70 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-a96ee81f5d16439b826fbbf00885b2c5
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07906653B2

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