Potassium Hydroxide → 3-methyl-2-[2-[[1-(5-methyl-1-trityl-1H-imidazol-4-yl)ethyl]amino]ethyl]indole

HRID 1657314노트

반응식

HRID 1657314 반응식
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4](S(C2C=CC=CC=2)(=O)=O)[C:3]=1[CH2:20][CH2:21][NH:22][CH:23]([C:25]1[N:26]=[CH:27][N:28]([C:31]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:29]=1[CH3:30])[CH3:24].[OH-].[K+]>CS(C)=O.O>[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]=1[CH2:20][CH2:21][NH:22][CH:23]([C:25]1[N:26]=[CH:27][N:28]([C:31]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)([C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)[C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[C:29]=1[CH3:30])[CH3:24]

참가 물질

5

반응물 2

HCID 14797Potassium HydroxideHCID 102588713-methyl-2-[2-[[1-(5-methyl-1-trityl-1H-imidazol-4-yl)ethyl]amino]ethyl]-1-phenylsulfonylindole

생성물 1

HCID 100297853-methyl-2-[2-[[1-(5-methyl-1-trityl-1H-imidazol-4-yl)ethyl]amino]ethyl]indole수율 79.9%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

반응 조건

온도
70 °C

실험 절차

A mixture of 3-methyl-2-[2-[[1-(5-methyl-1-trityl-1H-imidazol-4-yl)ethyl]amino]ethyl]-1-phenylsulfonylindole (970 mg) and powdered potassium hydroxide (819 mg) in dimethylsulfoxide (10 ml) were stirred at 70° C. for 1 hour. The resultant mixture was diluted with cold water and extracted twice with 30% tetrahydrofuran in 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% MeOH in chloroform) to give 3-methyl-2-[2-[[1-[5-methyl-1-trityl-1H-imidazol-4-yl)ethyl]amino]ethyl]indole (611.3 mg) as amorphous powder.

후처리

  1. extractionextracted twice with 30% tetrahydrofuran in ethyl acetate
  2. washThe extracts were washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was chromatographed on silica gel (eluted with 5% MeOH in chloroform)

출처 및 근거

ORD 기록
ord-0e34549162104b9f9131a745d5a81434
출처 데이터셋
uspto-grants-1993_10
특허 번호
US05256780

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