Trifluoroacetic acid → 4-[2-Anilino-1-(anilinocarbonyl)-2-oxoethyl]benzoic acid

HRID 1694831Notes

Reaction equation

HRID 1694831 reaction equation
[NH:1]([C:8](=[O:32])[CH:9]([C:19]1[CH:31]=[CH:30][C:22]([C:23]([O:25]C(C)(C)C)=[O:24])=[CH:21][CH:20]=1)[C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[NH:1]([C:8](=[O:32])[CH:9]([C:19]1[CH:20]=[CH:21][C:22]([C:23]([OH:25])=[O:24])=[CH:30][CH:31]=1)[C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59376446Tert-butyl 4-[2-anilino-1-(anilinocarbonyl)-2-oxoethyl]benzoate

Product 1

HCID 593764614-[2-Anilino-1-(anilinocarbonyl)-2-oxoethyl]benzoic acidYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-[2-anilino-1-(anilinocarbonyl)-2-oxoethyl]benzoate, prepared in the previous step, in CH2Cl2 (200 mL) at room temperature was added trifluoroacetic acid (50 mL). The reaction mixture was stirred at room temperature for 2 h and concentrated. The crude acid was dissolved in CH2Cl2, filtered, and precipitated with hexanes. The solid was collected by filtration, washed with hexanes, and dried under high vacuum to yield 4-[2-anilino-1-(anilinocarbonyl)-2-oxoethyl]benzoic acid (7.58 g, 71% from dimethyl [4-(tert-butoxycarbonyl)phenyl]malonate) as an off white solid: 1H NMR (600 MHz, DMSO-d6) δ 12.94 (s br, 1H), 10.26 (s br, 2H), 7.94 (d, J=8.2 Hz, 2H), 7.58 (d, J=7.6 Hz, 4H), 7.54 (d, J=8.2 Hz, 2H), 7.30 (t, J=7.6 Hz, 41-1), 7.05 (t, J=7.3 Hz, 2H), 4.97 (s, 1H); ESIMS calcd 375.1 (M++H), found 375.1 (M++H).

Workup

  1. concentrationconcentrated
  2. dissolutionThe crude acid was dissolved in CH2Cl2
  3. filtrationfiltered
  4. customprecipitated with hexanes
  5. filtrationThe solid was collected by filtration
  6. washwashed with hexanes
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-c0be64cf18e547d8812e4f5e53db3d4d
Source dataset
uspto-grants-2012_04
Patent number
US08158825B2

Reaction notes

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