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

HRID 29651

Reaction equation

HRID 29651 reaction equation
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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-aeddcc038b524471aa2618b1336daa7a
Source dataset
uspto-grants-2008_09
Patent number
US07420083B2

Linked notes

Loading…