Chloroform → HCID 178454302, Verbindung

HRID 1247790Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1247790
[C:1]([O:5][C:6]([N:8]=[C:9]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[NH:10][C:11]1[CH:15]=[N:14][N:13]2[CH2:16][CH2:17][NH:18][C:12]=12)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:27]1([C:33](Cl)([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(Cl)(Cl)Cl>N1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]=[C:9]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[NH:10][C:11]1[CH:15]=[N:14][N:13]2[CH2:16][CH2:17][N:18]([C:33]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)([C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)[C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:12]=12)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 6212ChloroformHCID 6456Trityl chlorideHCID 1784543037-[2,3-bis(tert-butoxycarbonyl)guanidino]-2,3-dihydro-1H-imidazo[1,2-b]pyrazole

Produkt 1

HCID 178454302HCID 178454302, VerbindungAusbeute 51,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of 7-[2,3-bis(tert-butoxycarbonyl)guanidino]-2,3-dihydro-1H-imidazo[1,2-b]pyrazole (1.83 g) in pyridine (10 ml) was added triphenylmethyl chloride (1.67 g). The mixture was stirred at 50° C. for 5 hours. After cooling, chloroform (50 ml) was added to the reaction mixture, and the mixture was washed successively with 10% aqueous citric acid solution, brine and saturated aqueous sodium hydrogen carbonate solution. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with 2% methanol/chloroform to give 7-[-2,3-bis(tert-butoxycarbonyl)guanidino]-1-triphenylmethyl-2,3-dihydro-1H-imidazo[1,2-b]pyrazole (1.57 g) as a solid.

Aufarbeitung

  1. temperatureAfter cooling
  2. washthe mixture was washed successively with 10% aqueous citric acid solution, brine and saturated aqueous sodium hydrogen carbonate solution
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel eluting with 2% methanol/chloroform

Quellen und Nachweise

ORD-Eintrag
ord-57eecb8ac85445bb9be2584f96bb2d08
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07129232B2

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