Trifluoroacetic acid → 3-Amino-4-benzyloxy-1-(2-fluorophenyl)pyrazole

HRID 968676Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 968676
C(O)(C(F)(F)F)=O.[CH2:8]([O:15][C:16]1[C:17]([NH:28]C(OC(C)(C)C)=O)=[N:18][N:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[F:27])[CH:20]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[OH-].[Na+]>C(Cl)(Cl)Cl.CCOC(C)=O>[NH2:28][C:17]1[C:16]([O:15][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:20][N:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[F:27])[N:18]=1

Komponenten

6

Edukt 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 691586054-Benzyloxy-3-(tert-butoxycarbonyl)amino-1-(2-fluorophenyl)pyrazole

Produkt 1

HCID 691586673-Amino-4-benzyloxy-1-(2-fluorophenyl)pyrazoleAusbeute 77,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

TFA (2 mL) was added to a solution of 4-benzyloxy-3-(tert-butoxycarbonyl)amino-1-(2-fluorophenyl)pyrazole (1.30 g) in CHCl3 (5 mL) at room temperature and the mixture was stirred for 1.5 hours at room temperature. After being neutralized with 5N NaOH, the mixture was diluted with EtOAc and washed with H2O, sat. NaHCO3 and brine. The organic layer was dried over anhydrous magnesium sulfate and concentrated in vacuo. The semicrystalline residue was triturated with hexane overnight and filtered to yield 742.6 mg of the title compound.

Aufarbeitung

  1. washwashed with H2O, sat. NaHCO3 and brine
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe semicrystalline residue was triturated with hexane overnight
  5. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-34e7bbb2286c47f9ae7499e3f4c32fac
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07304072B2

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