Water → 3-(6-{(3,5-Bis-trifluoromethyl-benzyl)-[2-(butyl-ethyl-amino)-5-trifluoromethyl-benzyl]-amino}-pyrimidin-4-ylamino)-propionic acid

HRID 604093Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 604093
[F:1][C:2]([F:50])([F:49])[C:3]1[CH:4]=[C:5]([CH:42]=[C:43]([C:45]([F:48])([F:47])[F:46])[CH:44]=1)[CH2:6][N:7]([CH2:24][C:25]1[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:27][C:26]=1[N:35]([CH2:38][CH2:39][CH2:40][CH3:41])[CH2:36][CH3:37])[C:8]1[N:13]=[CH:12][N:11]=[C:10]([NH:14][CH2:15][CH2:16][C:17]([O:19]C(C)(C)C)=[O:18])[CH:9]=1.O.C(=O)(O)[O-].[Na+]>Cl.C(OCC)(=O)C>[F:50][C:2]([F:1])([F:49])[C:3]1[CH:4]=[C:5]([CH:42]=[C:43]([C:45]([F:46])([F:47])[F:48])[CH:44]=1)[CH2:6][N:7]([CH2:24][C:25]1[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:27][C:26]=1[N:35]([CH2:38][CH2:39][CH2:40][CH3:41])[CH2:36][CH3:37])[C:8]1[N:13]=[CH:12][N:11]=[C:10]([NH:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])[CH:9]=1

Komponenten

6

Edukt 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 86626846Tert-butyl 3-(6-{(3,5-bis-trifluoromethyl-benzyl)-[2-(butyl-ethyl-amino)-5-trifluoromethyl-benzyl]-amino}-pyrimidin-4-ylamino)-propionate

Produkt 1

HCID 866268473-(6-{(3,5-Bis-trifluoromethyl-benzyl)-[2-(butyl-ethyl-amino)-5-trifluoromethyl-benzyl]-amino}-pyrimidin-4-ylamino)-propionic acidAusbeute 103 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

Tert-butyl 3-(6-{(3,5-bis-trifluoromethyl-benzyl)-[2-(butyl-ethyl-amino)-5-trifluoromethyl-benzyl]-amino}-pyrimidin-4-ylamino)-propionate (60 mg) is dissolved in a 4N-hydrochloric acid in ethyl acetate (0.5 ml) and the mixture is stirred at room temperature for 1.5 hours. To the reaction solution are added ethyl acetate and water, and followed by a further addition of a saturated aqueous sodium bicarbonate solution to make the pH of aqueous layer to be about 4, and the mixture is separated. The organic layer is washed with a saturated brine, dried over magnesium sulfate and the mixture is concentrated under reduced pressure to give 3-(6-{(3,5-bis-trifluoromethyl-benzyl)-[2-(butyl-ethyl-amino)-5-trifluoromethyl-benzyl]-amino}-pyrimidin-4-ylamino)-propionic acid (57 mg). MS (m/z): 666 [M+H]+

Aufarbeitung

  1. customthe mixture is separated
  2. washThe organic layer is washed with a saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationthe mixture is concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b8343cbbf1f74bde8bf7278c10950c97
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07906517B2

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