Trityl chloride → HCID 21904528, Verbindung

HRID 1247796Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1247796
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[OH:13][CH2:14][CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20].C(N(C(C)C)C(C)C)C.S(=O)(=O)(O)O.[NH2:38][C:39]1[CH:40]=[N:41][N:42]([CH3:45])[C:43]=1[NH2:44].[C:46](Cl)([C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)([C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1>C(Cl)(Cl)Cl.C(N(CC)CC)C>[C:19]([O:18][C:17]([NH:16][CH2:15][CH2:14][O:13][C:1]([NH:38][C:39]1[CH:40]=[N:41][N:42]([CH3:45])[C:43]=1[NH:44][C:46]([C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1)([C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)=[O:2])=[O:23])([CH3:20])([CH3:22])[CH3:21]

Komponenten

8

Edukt 5

HCID 6456Trityl chlorideHCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 2733206tert-butyl N-(2-hydroxyethyl)carbamateHCID 219045711H-Pyrazole, 4,5-diamine-1-methyl-, sulfate (1:1)

Produkt 1

HCID 21904528HCID 21904528, VerbindungAusbeute 29,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittel2×HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a suspension of 1,1′-carbonyldiimidazole (2.0 g) in dehydrated chloroform (30 ml) was added a solution of tert-butyl N-(2-hydroxyethyl)carbamate (1.92 g) in dehydrated chloroform (10 ml) under ice-cooling, and the mixture was stirred at room temperature for 1 hour. To the reaction mixture were added N-ethyldiisopropylamine (2.2 ml) and 4,5-diamino-1-methylpyrazole sulfuric acid salt (2.58 g), and the mixture was stirred at room temperature for 17.5 hours. To the reaction mixture were added trityl chloride (3.42 g) and triethylamine (1.25 g). The mixture was stirred at room temperature for 2 hours. The reaction mixture was washed 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 5% methanol/chloroform to give 4-{[2-(tert-butoxycarbonylamino)ethoxycarbonyl]amino}-5-(tritylamino)-1-methylpyrazole (1.91 g) as a solid.

Aufarbeitung

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 17.5 hours
  3. stirringThe mixture was stirred at room temperature for 2 hours
  4. washThe reaction mixture was washed with 10% aqueous citric acid solution, brine and saturated aqueous sodium hydrogen carbonate solution
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography on silica gel eluting with 5% methanol/chloroform

Quellen und Nachweise

ORD-Eintrag
ord-4f52cf45ab19466eb71d41d41521af00
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07129232B2

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