Hydrochloric Acid → HCID 57972811, Verbindung

HRID 661459Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 661459
C([O:3][C:4](=[O:10])[CH2:5][C@H:6]([NH2:9])[CH2:7][CH3:8])C.Br[C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].Cl>[Cu](I)I.C(OCC)(=O)C.O.CN(C)C=O>[F:19][C:18]([F:21])([F:20])[C:15]1[CH:16]=[CH:17][C:12]([NH:9][C@H:6]([CH2:7][CH3:8])[CH2:5][C:4]([OH:3])=[O:10])=[CH:13][CH:14]=1

Komponenten

9

Edukt 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 67872Benzene, 1-bromo-4-(trifluoromethyl)-HCID 11788640HCID 11788640, Verbindung

Produkt 1

HCID 57972811HCID 57972811, VerbindungAusbeute 40,3 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 83717Copper iodideKatalysatorHCID 962WaterLösungsmittel2×HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

(R)-3-Aminovaleric acid ethyl ester (0.5 g), 4-bromobenzotrifluoride (0.62 g), copper iodide (0.053 g), potassium carbonate (1.14 g) and water (0.5 ml) were added to dimethylformamide (5 ml) and the mixture was sealed under nitrogen atmosphere and stirred at 100° C. for 3 days. The mixture was cooled, water and ethyl acetate were added to the mixture, and the pH of the mixture was adjusted to about 3 or less with addition of 2N HCl. The organic layer was separated, dried over magnesium sulfate and concentrated at reduced pressure. The resulting residue was purified by column chromatography to give the titled compound (0.29 g, yield 40.3%). MS (APCI) m/z: 262 [M+H]+.

Aufarbeitung

  1. customthe mixture was sealed under nitrogen atmosphere
  2. temperatureThe mixture was cooled
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated at reduced pressure
  6. customThe resulting residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-fa6ec3c00cb0478f81e8cf7948ef838a
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08084611B2

Notizen zur Reaktion

Wird geladen…