Water → tert-butyl ((3S)-3-hydroxy-4-{[1-(2-hydroxyethyl)-5-(tritylamino)-1H-pyrazol-4-yl]amino}-4-oxobutyl)carbamate

HRID 459627Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 459627
[NH2:1][C:2]1[N:6]([CH2:7][CH2:8][OH:9])[N:5]=[CH:4][C:3]=1[NH:10][C:11](=[O:24])[C@@H:12]([OH:23])[CH2:13][CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19].[C:25](Cl)([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(N(CC)CC)C.O>CN(C)C=O>[OH:23][C@H:12]([C:11]([NH:10][C:3]1[CH:4]=[N:5][N:6]([CH2:7][CH2:8][OH:9])[C:2]=1[NH:1][C:25]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)=[O:24])[CH2:13][CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:19])[CH3:20]

Komponenten

6

Edukt 4

HCID 962WaterHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 69652223tert-butyl ((3S)-4-{[5-amino-1-(2-hydroxyethyl)-1H-pyrazol-4-yl]amino}-3-hydroxy-4-oxobutyl)carbamate

Produkt 1

HCID 69651947tert-butyl ((3S)-3-hydroxy-4-{[1-(2-hydroxyethyl)-5-(tritylamino)-1H-pyrazol-4-yl]amino}-4-oxobutyl)carbamateAusbeute 71,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl ((3S)-4-{[5-amino-1-(2-hydroxyethyl)-1H-pyrazol-4-yl]amino}-3-hydroxy-4-oxobutyl)carbamate (2.86 g) in N,N-dimethylformamide (30 ml) were added trityl chloride (3.48 g) and triethylamine (3.48 ml), and the mixture was stirred overnight at room temperature. Water was added to the reaction mixture, and the whole mixture was extracted with ethyl acetate. The extract was washed with water and brine and dried over anhydrous magnesium sulfate. Evaporation of the solvent under reduced pressure gave crude crystals, which were washed with ethyl acetate-diisopropyl ether (2:1) and collected by filtration to give tert-butyl ((3S)-3-hydroxy-4-{[1-(2-hydroxyethyl)-5-(tritylamino)-1H-pyrazol-4-yl]amino}-4-oxobutyl)carbamate (3.5 g).

Aufarbeitung

  1. extractionthe whole mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customEvaporation of the solvent under reduced pressure
  5. customgave crude crystals, which
  6. washwere washed with ethyl acetate-diisopropyl ether (2:1)
  7. filtrationcollected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-487dfd716e6e4b4c8330aeb69dfd01e2
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07192943B2

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