Water → rac-Ethyl 5-[(2-{5-fluoro-2-[(4-{2-[4-(trifluoromethyl)phenyl]ethyl}benzyl)oxy]phenyl}ethyl)-amino]-5,6,7,8-tetrahydroquinoline-2-carboxylate

HRID 875351Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 875351
Cl.Cl.[F:3][C:4]1[CH:5]=[CH:6][C:7]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][C:33]([CH2:36][CH2:37][C:38]3[CH:43]=[CH:42][C:41]([C:44]([F:47])([F:46])[F:45])=[CH:40][CH:39]=3)=[CH:32][CH:31]=2)=[C:8]([CH2:10][CH2:11][NH:12][CH:13]2[CH2:22][CH2:21][CH2:20][C:19]3[N:18]=[C:17]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:16]=[CH:15][C:14]2=3)[CH:9]=1.C(N(CC)CC)C.C(OCC)(=O)C.O>C1COCC1>[F:3][C:4]1[CH:5]=[CH:6][C:7]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][C:33]([CH2:36][CH2:37][C:38]3[CH:39]=[CH:40][C:41]([C:44]([F:47])([F:45])[F:46])=[CH:42][CH:43]=3)=[CH:32][CH:31]=2)=[C:8]([CH2:10][CH2:11][NH:12][CH:13]2[CH2:22][CH2:21][CH2:20][C:19]3[N:18]=[C:17]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:16]=[CH:15][C:14]2=3)[CH:9]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 90024533rac-Ethyl 5-[(2-{5-fluoro-2-[(4-{2-[4-(trifluoromethyl)phenyl]ethyl}benzyl)oxy]phenyl}ethyl)-amino]-5,6,7,8-tetrahydroquinoline-2-carboxylate dihydrochloride

Produkt 1

HCID 89950578rac-Ethyl 5-[(2-{5-fluoro-2-[(4-{2-[4-(trifluoromethyl)phenyl]ethyl}benzyl)oxy]phenyl}ethyl)-amino]-5,6,7,8-tetrahydroquinoline-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

479 mg (0.64 mmol) of rac-ethyl 5-[(2-{5-fluoro-2-[(4-{2-[4-(trifluoromethyl)phenyl]ethyl}-benzyl)oxy]phenyl}ethyl)amino]-5,6,7,8-tetrahydroquinoline-2-carboxylate dihydrochloride (Example 158A) were taken up in 4.7 ml of THF, 0.27 ml of triethylamine was added and the mixture was stirred at room temperature for one hour. Ethyl acetate and water were then added to the reaction solution, the phases were separated and the aqueous phase was extracted once more with ethyl acetate. The combined organic phases were again washed with water, dried over magnesium sulphate, filtered and then concentrated to dryness. This gave 383 mg (0.62 mmol, 96% of theory) of the target compound.

Aufarbeitung

  1. customthe phases were separated
  2. extractionthe aqueous phase was extracted once more with ethyl acetate
  3. washThe combined organic phases were again washed with water
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-c7c924f66cd249a194bda7cfa67e7cc9
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08981104B2

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