Trifluoroacetic acid → C-{2-methyl-5-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-furan-3-yl}-methylamine

HRID 68580

Reaktionsgleichung

Reaktionsgleichung von HRID 68580
FC(F)(F)C(O)=O.C(OC(=O)[NH:14][CH2:15][C:16]1[CH:20]=[C:19]([C:21]2[CH2:25][C:24]([C:30]3[CH:35]=[C:34]([Cl:36])[C:33]([Cl:37])=[C:32]([Cl:38])[CH:31]=3)([C:26]([F:29])([F:28])[F:27])[O:23][N:22]=2)[O:18][C:17]=1[CH3:39])(C)(C)C.[OH-].[Na+]>ClCCl>[CH3:39][C:17]1[O:18][C:19]([C:21]2[CH2:25][C:24]([C:30]3[CH:35]=[C:34]([Cl:36])[C:33]([Cl:37])=[C:32]([Cl:38])[CH:31]=3)([C:26]([F:28])([F:27])[F:29])[O:23][N:22]=2)=[CH:20][C:16]=1[CH2:15][NH2:14]

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 86706654{2-Methyl-5-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-furan-3-ylmethyl}-carbamic acid tert-butyl ester

Produkt 1

HCID 86706655C-{2-methyl-5-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-furan-3-yl}-methylamineAusbeute 98,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Trifluoroacetic acid (6.0 ml) is added to a solution of {2-methyl-5-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-furan-3-ylmethyl}-carbamic acid tert-butyl ester (2.05 g) in dichloromethane (20 ml). After 45 min at room temperature, an aqueous solution of NaOH (2M) is added until pH 12 is reached and the reaction mixture is extracted three times with dichloromethane. The combined organic phases are washed with a saturated solution of NaCl, dried over Na2SO4 and concentrated in vacuo to yield C-{2-methyl-5-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-furan-3-yl}-methylamine (1.64 g, compound 2.5 in Table 2) as a light yellow foam. The crude product obtained is used without further purification. MS (HPLC/MS): 410 (MH), Retention time: 1.27 min.

Aufarbeitung

  1. extractionthe reaction mixture is extracted three times with dichloromethane
  2. washThe combined organic phases are washed with a saturated solution of NaCl
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a3d259fbdfa2492fa1f1c34f1efc80a0
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822466B2

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