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Cesium carbonate → 5-(4-tert-Butoxycarbonyl-[1,4]diazepane-1-carbonyl)-1-isopropyl-1H-indole-2-carboxylic acid ethyl ester

HRID 1992493
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인쇄 미리보기

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HRID 1992493 반응식
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([C:15]([N:17]1[CH2:23][CH2:22][CH2:21][N:20]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:19][CH2:18]1)=[O:16])=[CH:10][CH:9]=2)=[O:5])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[CH:37](CS([O-])(=O)=O)([CH3:39])[CH3:38]>C(#N)C>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH:37]([CH3:39])[CH3:38])[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([C:15]([N:17]1[CH2:23][CH2:22][CH2:21][N:20]([C:24]([O:26][C:27]([CH3:29])([CH3:28])[CH3:30])=[O:25])[CH2:19][CH2:18]1)=[O:16])=[CH:10][CH:9]=2)=[O:5])[CH3:2]
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참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 22141912Isopropyl-methanesulfonateHCID 685368405-(4-tert-butoxycarbonyl-[1,4]diazepane-1-carbonyl)-1H-indole-2-carboxylic acid ethyl ester

생성물 1

HCID 685367535-(4-tert-Butoxycarbonyl-[1,4]diazepane-1-carbonyl)-1-isopropyl-1H-indole-2-carboxylic acid ethyl ester수율 99.9%

시약·촉매·용매 1

HCID 6342
Acetonitrile
용매

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온도
95 °C

실험 절차

To a solution of 5-(4-tert-butoxycarbonyl-[1,4]diazepane-1-carbonyl)-1H-indole-2-carboxylic acid ethyl ester (1.55 g, 3.5 mmol) in acetonitrile (25 ml) under an argon atmosphere were added caesium carbonate (2 eq., 2.44 g) and isopropylmethanesulfonate (2 eq., 1.03 g). The mixture was heated at 95° C. (oil-bath temperature) overnight. The mixture was cooled to room temperature and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel (3:1 heptane/ethyl acetate eluant) to afford the product as a light-brown oil (1.6 g, 93%). MS (m/z): 458.3 (M+H)+.

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. customevaporated under reduced pressure
  3. customThe crude product was purified by column chromatography on silica gel (3:1 heptane/ethyl acetate eluant)

출처 및 근거

ORD 기록
ord-f7720254379a46edacf8c8e8d13001fe
출처 데이터셋
uspto-grants-2010_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07648979B2

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