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Benzene → 3-methyl-2-[2-[[1-(5-methyl-1-trityl-1H-imidazol-4-yl)ethyl]amino]ethyl]-1-phenylsulfonylindole

HRID 1657323
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HRID 1657323 반응식
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])[CH:3]=1.[NH2:20][CH:21]([C:23]1[N:24]=[CH:25][N:26]([C:29]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:27]=1[CH3:28])[CH3:22].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].[CH:56]1C=CC=C[CH:57]=1>O>[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])[C:3]=1[CH2:56][CH2:57][NH:20][CH:21]([C:23]1[N:24]=[CH:25][N:26]([C:29]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[C:27]=1[CH3:28])[CH3:22]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 5

HCID 241BenzeneHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 104066724-(1-aminoethyl)-5-methyl-1-trityl-1H-imidazoleHCID 105727373-methyl-1-(phenylsulfonyl)-1H-indole

생성물 1

HCID 102588713-methyl-2-[2-[[1-(5-methyl-1-trityl-1H-imidazol-4-yl)ethyl]amino]ethyl]-1-phenylsulfonylindole

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of 2-[2-methanesulfonyloxy)ethyl]-3-methyl-1-(benzenesulfonyl)indole (4.32 g), (-)-4-(1-aminoethyl)-5-methyl-1-trityl-1H-imidazole (3.67 g), sodium iodide (456 mg) and potassium carbonate [1.51 g) in benzene (43 ml) was stirred at reflux for 24 hours. The reaction mixture was diluted with cold water and extracted twice with ethyl acetate. The extracts were washed with brine, dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel (eluted with 5% methanol in chloroform) to give (-)-3-methyl-2-[2-[[1-(5-methyl-1-trityl-1H-imidazol-4-yl)ethyl]amino]ethyl]-1-(benzenesulfonyl)indole (4.82 g) as amorphous powder.

후처리

  1. temperatureat reflux for 24 hours
  2. extractionextracted twice with ethyl acetate
  3. washThe extracts were washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was chromatographed on silica gel (eluted with 5% methanol in chloroform)

출처 및 근거

ORD 기록
ord-8311d7f5771846edbb7f073ba33ccab5
출처 데이터셋
uspto-grants-1993_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05256780

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