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

HRID 1657324Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1657324
[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]

Komponenten

5

Edukt 2

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

Produkt 1

HCID 100297853-methyl-2-[2-[[1-(5-methyl-1-trityl-1H-imidazol-4-yl)ethyl]amino]ethyl]indoleAusbeute 79,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of (-)-3-methyl-2-[2-[[1-(5-methyl-1-trityl-1H-imidazol-4-yl)ethyl]amino]ethyl]-1-(benzenesulfonyl)indole (4.6 g) and powdered potassium hydroxide (3.9 g) in dimethyl sulfoxide (46 ml) were stirred at 70° C. for 1 hour. The resultant mixture was diluted with cold water and extracted twice with a mixture of ethyl acetate-tetrahydrofuran (1:1, V/V). 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]indole (2.9 g) as amorphous powder.

Aufarbeitung

  1. extractionextracted twice with a mixture of ethyl acetate-tetrahydrofuran (1:1, V/V)
  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% methanol in chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-8fe093c467a84ddf89b6606993589488
Quelldatensatz
uspto-grants-1993_10
Patentnummer
US05256780

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