Hydrochloric Acid → 3-[[4-Methoxy-2′-(trifluoromethyl)[1,1′-biphenyl]-3-yl]oxy]azetidine

HRID 1850080Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1850080
[C:1]([O:5]C([N:8]1[CH2:11][CH:10]([O:12][C:13]2[CH:14]=[C:15]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]([F:30])([F:29])[F:28])[CH:16]=[CH:17][C:18]=2[O:19][CH3:20])[CH2:9]1)=O)(C)(C)C.Cl.C([O-])(O)=O.[Na+]>CCOC(C)=O.O1CCOCC1>[NH3:8].[CH3:1][OH:5].[CH3:20][O:19][C:18]1[CH:17]=[CH:16][C:15]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]([F:30])([F:29])[F:28])=[CH:14][C:13]=1[O:12][CH:10]1[CH2:9][NH:8][CH2:11]1

Komponenten

7

Edukt 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 67342335HCID 67342335, Verbindung

Produkt 2

HCID 21705897Ammonia methanolAusbeute 10 %HCID 461964483-[[4-Methoxy-2′-(trifluoromethyl)[1,1′-biphenyl]-3-yl]oxy]azetidineAusbeute 122,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To title compound of Step E (0.062 g, 0.146 mmol) in EtOAc (2 mL) was added 4M HCl in dioxane (2 mL). After 18 h, the reaction was neutralized with saturated NaHCO3 (aq.) and extracted with CH2Cl2 (2×). The combined organics were dried and concentrated. Silica gel chromatography (10-80% 2M NH3/MeOH in CH2Cl2) gave 0.029 g (61%) of the title compound. MS (ESI): mass calcd. for C17H16F3NO2, 323.11. m/z found, 324.2 [M+H]+. 1H NMR (CDCl3): 7.73 (d, J=7.8 Hz, 1H), 7.54 (t, J=7.3 Hz, 1H), 7.45 (t, J=7.6 Hz, 1H), 7.32 (d, J=7.6 Hz, 1H), 6.90 (td, J=8.2, 5.1 Hz, 2H), 6.59 (s, 1H), 5.02-4.97 (m, 1H), 3.92 (s, 3H), 3.96-3.85 (m, 7H).

Aufarbeitung

  1. extractionextracted with CH2Cl2 (2×)
  2. customThe combined organics were dried
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-8bf33b46c60b463084aa58ee5a6f091d
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08957059B2

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