Sulfuric Acid → 1-[4-(2.2.2-Trifluoro-ethanesulfonylamino)-benzyl]-5-(2-oxo-propyl)-1H-indole-2-carboxylic Acid Ethyl Ester

HRID 342808노트

반응식

HRID 342808 반응식
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([NH:29][S:30]([CH2:33][C:34]([F:37])([F:36])[F:35])(=[O:32])=[O:31])=[CH:25][CH:24]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([CH2:15][C:16]1([CH3:21])OCC[O:17]1)=[CH:10][CH:9]=2)=[O:5])[CH3:2].S(=O)(=O)(O)O>CC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([NH:29][S:30]([CH2:33][C:34]([F:37])([F:36])[F:35])(=[O:32])=[O:31])=[CH:25][CH:24]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([CH2:15][C:16](=[O:17])[CH3:21])=[CH:10][CH:9]=2)=[O:5])[CH3:2]

참가 물질

4

반응물 2

HCID 1118Sulfuric AcidHCID 675985121-[4-(2,2,2-trifluoro-ethanesulfonylamino)-benzyl]-5-(2-methyl-[1,3]dioxolan-2-ylmethyl)-1H-indole-2-carboxylic acid ethyl ester

생성물 1

HCID 675993131-[4-(2.2.2-Trifluoro-ethanesulfonylamino)-benzyl]-5-(2-oxo-propyl)-1H-indole-2-carboxylic Acid Ethyl Ester수율 59.6%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

To a solution of crude 1-[4-(2,2,2-trifluoro-ethanesulfonylamino)-benzyl]-5-(2-methyl-[1,3]dioxolan-2-ylmethyl)-1H-indole-2-carboxylic acid ethyl ester (2.85 g, ≈5 mmol) in acetone (60 ml) was added concentrated sulfuric acid (0.6 ml). The solution was stirred at room temperature for about 45 minutes, and most of the solvent was removed under reduced pressure. The residue was taken up in ethyl acetate, washed with water and brine, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by flash chromatography (silica, 130 g) eluting with a gradient from 30% -ethyl acetate/hexane to 40% ethyl acetate/hexane, to give the title compound (1.48 g).

후처리

  1. custommost of the solvent was removed under reduced pressure
  2. washwashed with water and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (silica, 130 g)
  6. washeluting with a gradient from 30% -ethyl acetate/hexane to 40% ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-8f2bc46890764eacaba2817c227374ca
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05859044

반응 노트

불러오는 중…