tert-Butanol → 4-Benzyloxy-3-(tert-butoxycarbonyl)amino-1-(2-fluorophenyl)pyrazole

HRID 968675Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 968675
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:8])C=CC=CC=1.[CH2:18]([O:25][C:26]1[C:27](C(O)=O)=[N:28][N:29]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[F:37])[CH:30]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C([N:43]([CH2:46]C)CC)C.[CH3:48][C:49]([OH:52])([CH3:51])[CH3:50]>O1CCOCC1.CCOC(C)=O>[CH2:18]([O:25][C:26]1[C:27]([NH:43][C:46]([O:52][C:49]([CH3:51])([CH3:50])[CH3:48])=[O:8])=[N:28][N:29]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[F:37])[CH:30]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Komponenten

7

Edukt 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 69159267HCID 69159267, Verbindung

Produkt 1

HCID 691586054-Benzyloxy-3-(tert-butoxycarbonyl)amino-1-(2-fluorophenyl)pyrazole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Diphenylphosphoryl azide (2.16 mL) was added to a mixture of 4-benzyloxy-1-(2-fluorophenyl)pyrazole-3-carboxylic acid (2.09 g) and triethylamine (1.39 mL) in a mixture of 1,4-dioxane (25 mL) and tBuOH (25 mL). The mixture was refluxed for 1 hour and cooled to room temperature. The mixture was diluted with EtOAc and washed with H2O, 10% aq. citric acid, sat. NaHCO3 and brine. The organic layer was dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (EtOAc/hexane 1/19, 1/9, 1/4 and 1/2) to yield 1.30 g of the title compound.

Aufarbeitung

  1. temperatureThe mixture was refluxed for 1 hour
  2. washwashed with H2O, 10% aq. citric acid, sat. NaHCO3 and brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography on silica gel (EtOAc/hexane 1/19, 1/9, 1/4 and 1/2)

Quellen und Nachweise

ORD-Eintrag
ord-6099d9d1ff0542e6ae4939ec054f48a1
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07304072B2

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