Hydrochloric Acid → 4-{4-[5-Cyclopropyl-3-(2,6-dichloro-phenyl)-isoxazol-4-ylmethoxy]-azepan-1-yl}-benzoic acid

HRID 1689826Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1689826
C([O:3][C:4](=[O:36])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:17][CH2:16][CH2:15][CH:14]([O:18][CH2:19][C:20]3[C:21]([C:28]4[C:33]([Cl:34])=[CH:32][CH:31]=[CH:30][C:29]=4[Cl:35])=[N:22][O:23][C:24]=3[CH:25]3[CH2:27][CH2:26]3)[CH2:13][CH2:12]2)=[CH:7][CH:6]=1)C.[OH-].[K+].Cl>C(O)C.O1CCCC1>[CH:25]1([C:24]2[O:23][N:22]=[C:21]([C:28]3[C:29]([Cl:35])=[CH:30][CH:31]=[CH:32][C:33]=3[Cl:34])[C:20]=2[CH2:19][O:18][CH:14]2[CH2:15][CH2:16][CH2:17][N:11]([C:8]3[CH:7]=[CH:6][C:5]([C:4]([OH:36])=[O:3])=[CH:10][CH:9]=3)[CH2:12][CH2:13]2)[CH2:27][CH2:26]1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 59369326HCID 59369326, Verbindung

Produkt 1

HCID 252047654-{4-[5-Cyclopropyl-3-(2,6-dichloro-phenyl)-isoxazol-4-ylmethoxy]-azepan-1-yl}-benzoic acidAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 8.28 g (15.64 mmol) of 4-{4-[5-Cyclopropyl-3-(2,6-dichloro-phenyl)-isoxazol-4-ylmethoxy]-azepan-1-yl}-benzoic acid ethyl ester (Isomer B) in 50 mL of Ethanol and 150 mL of tetrahydrofuran, is added potassium hydroxide (55.16 g, 78.19 mmol). The resulting mixture is stirred at 60° C. for 14 hours. The mixture is cooled to room temperature and acidified with 2N HCl to pH 5-6. The solvent is removed under vacuum, the resulting slurry is diluted with CH2Cl2 (150 mL) and washed with water (2×80 mL). The organic layer is dried (MgSO4), filtered and concentrated to afford 7.76 g of the title compound as a white solid (98%). MS (m/e): 501 (M+1).

Aufarbeitung

  1. temperatureThe mixture is cooled to room temperature
  2. customThe solvent is removed under vacuum
  3. additionthe resulting slurry is diluted with CH2Cl2 (150 mL)
  4. washwashed with water (2×80 mL)
  5. dry with materialThe organic layer is dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-2604137ef5874f38928870656924b27c
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153624B2

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