Trifluoroacetic acid → 4-[2-[(E)-(4-tert-butylphenyl)methylideneamino]oxyethoxy]-2-[4-(trifluoromethyl)benzoyl]oxybenzoic acid

HRID 29651

Reaktionsgleichung

Reaktionsgleichung von HRID 29651
C([O:5][C:6](=[O:42])[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][O:16]/[N:17]=[CH:18]/[C:19]2[CH:24]=[CH:23][C:22]([C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:21][CH:20]=2)=[CH:9][C:8]=1[O:29][C:30](=[O:41])[C:31]1[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:33][CH:32]=1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl.[Cl-].[Na+].O>[C:25]([C:22]1[CH:23]=[CH:24][C:19](/[CH:18]=[N:17]/[O:16][CH2:15][CH2:14][O:13][C:10]2[CH:11]=[CH:12][C:7]([C:6]([OH:42])=[O:5])=[C:8]([O:29][C:30](=[O:41])[C:31]3[CH:32]=[CH:33][C:34]([C:37]([F:39])([F:40])[F:38])=[CH:35][CH:36]=3)[CH:9]=2)=[CH:20][CH:21]=1)([CH3:28])([CH3:26])[CH3:27]

Komponenten

5

Edukt 2

HCID 6422Trifluoroacetic acidHCID 87734367tert-butyl 4-[2-[(E)-(4-tert-butylphenyl)methylideneamino]oxyethoxy]-2-[4-(trifluoromethyl)benzoyl]oxybenzoate

Produkt 1

HCID 111568084-[2-[(E)-(4-tert-butylphenyl)methylideneamino]oxyethoxy]-2-[4-(trifluoromethyl)benzoyl]oxybenzoic acidAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

To a solution of 4-{2-[({(E)-[4-(tert-butyl)phenyl]methylidene}amino)oxy]ethoxy}-2-{[4-(trifluoromethyl)benzoyl]oxy}benzoic acid tert-butyl ester (0.387 g, 0.66 mmol) in methylene chloride (15 mL) was added trifluoroacetic acid (0.400 mL, 2.83 mmol). The reaction was stirred at room temperature overnight, poured into brine and the aqueous layer extracted with ethyl acetate. The combined organics dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by flash chromatography using ethyl acetate/hexanes (20/80)+1% formic acid to afford the title compound (0.300 g, 86%) as a white solid. mp=146.3-147.9° C.; mass spectrum (+APCI, M+H) m/z 530. 1H NMR (400 MHz, DMSO-d6); δ 12.70 (bs, 1H), 8.28 (d, 2H), 8.24 (s, 1H), 7.95 (m, 3H), 7.52 (d, 2H), 7.40 (d, 2H), 7.03 (m, 2H), 4.44 (t, 2H), 4.38 (t, 2H), 1.26 (s, 9H). Elemental analysis: Calcd. for C28H26F3NO6: C, 63.51; H, 4.95; N, 2.65, Found: C, 63.15; H, 4.90; N, 2.64.

Aufarbeitung

  1. extractionthe aqueous layer extracted with ethyl acetate
  2. dry with materialThe combined organics dried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-aeddcc038b524471aa2618b1336daa7a
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07420083B2

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