Trifluoroacetic acid → 3-(4-{[(2-(2,4-Dimethylphenyl)amino-2-oxoethyl)(2-furylmethyl)amino]methyl}-phenyl)-2,2-dimethylpropionic acid

HRID 353172Notes

Reaction equation

HRID 353172 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:37])[CH2:11][N:12]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][C:27]([CH3:36])([CH3:35])[C:28]([O:30]C(C)(C)C)=[O:29])=[CH:22][CH:21]=1)[CH2:13][C:14]1[O:15][CH:16]=[CH:17][CH:18]=1.FC(F)(F)C(O)=O>ClCCl>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:37])[CH2:11][N:12]([CH2:19][C:20]1[CH:21]=[CH:22][C:23]([CH2:26][C:27]([CH3:35])([CH3:36])[C:28]([OH:30])=[O:29])=[CH:24][CH:25]=1)[CH2:13][C:14]1[O:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22708241Tert-butyl 3-(4-{[(2-(2,4-dimethylphenyl)amino-2-oxoethyl)(2-furylmethyl)amino]methyl}phenyl)-2,2-dimethylpropionate

Product 1

HCID 227081953-(4-{[(2-(2,4-Dimethylphenyl)amino-2-oxoethyl)(2-furylmethyl)amino]methyl}-phenyl)-2,2-dimethylpropionic acidYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 192 mg (0.380 mmol) of tert-butyl 3-(4-{[(2-(2,4-dimethylphenyl)-amino-2-oxoethyl)(2-furylmethyl)amino]methyl}phenyl)-2,2-dimethylpropionate (Example 1-1) in 1 ml of dichloromethane is treated with 1 ml of trifluoroacetic acid and stirred at room temperature for 2 h. The mixture is then concentrated under reduced pressure, the residue is taken up in ethyl acetate and the organic phase is washed 2× with water, 1× with 20% strength sodium acetate solution, 1× with water and 1× with sat. NaCl solution, dried over sodium sulphate and freed from the solvent under reduced pressure. Chromatographic purification of the residue on silica gel (dichloromethane→dichloromethane/methanol 20:1) gives 150 mg (88%) of 3-(4-{[(2-(2,4-dimethylphenyl)amino-2-oxoethyl)(2-furylmethyl)amino]methyl}phenyl)-2,2-dimethylpropionic acid.

Workup

  1. concentrationThe mixture is then concentrated under reduced pressure
  2. washthe organic phase is washed 2× with water, 1× with 20% strength sodium acetate solution, 1× with water and 1× with sat. NaCl solution
  3. dry with materialdried over sodium sulphate
  4. customChromatographic purification of the residue on silica gel (dichloromethane→dichloromethane/methanol 20:1)

Sources & evidence

ORD record
ord-068a8af87a224b26981a5cc27a1ac41e
Source dataset
uspto-grants-2004_06
Patent number
US06750236B2

Reaction notes

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