Trifluoroacetic acid → 4-{2-[6-(4-Tert-butylbenzenesulfonylamino)-5-(4-methylphenyl)pyrimidin-4-yloxy]ethoxy}phenoxyacetic acid

HRID 1082284

Reaction equation

HRID 1082284 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[N:20]=[CH:19][N:18]=[C:17]([O:21][CH2:22][CH2:23][O:24][C:25]3[CH:39]=[CH:38][C:28]([O:29][CH2:30][C:31]([O:33]C(C)(C)C)=[O:32])=[CH:27][CH:26]=3)[C:16]=2[C:40]2[CH:45]=[CH:44][C:43]([CH3:46])=[CH:42][CH:41]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>ClCCl>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([S:11]([NH:14][C:15]2[N:20]=[CH:19][N:18]=[C:17]([O:21][CH2:22][CH2:23][O:24][C:25]3[CH:39]=[CH:38][C:28]([O:29][CH2:30][C:31]([OH:33])=[O:32])=[CH:27][CH:26]=3)[C:16]=2[C:40]2[CH:45]=[CH:44][C:43]([CH3:46])=[CH:42][CH:41]=2)(=[O:13])=[O:12])=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 23362083Tert-butyl 4-{2-(6-(4-tert-butybenzenesulfonylamino)-5-(4-methylphenyl)pyrimidin-4-yloxy)ethoxy}phenoxyacetate

Product 1

HCID 196894584-{2-[6-(4-Tert-butylbenzenesulfonylamino)-5-(4-methylphenyl)pyrimidin-4-yloxy]ethoxy}phenoxyacetic acidYield 99.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-{2-{6-(4-tert-butylbenzenesulfonylamino)-5-(4-methylphenyl)pyrimidin-4-yloxy]ethoxy}phenoxyacetate (1.25 g) in dichloromethane (120 ml) are added anisole (2.09 g) and trifluoroacetic acid (20 ml) under ice-cooling. The mixture is stirred at room temperature for five hours, washed with water, and extracted with 10% aqueous sodium hydroxide solution. The aqueous layer is washed with chloroform, and acidified with 10% hydrochloric acid under ice-cooling. The mixture is extracted with ethyl acetate, and the extract is washed, dried, and evaporated to remove the solvent. The residue is crystallized from ethyl acetate/diisopropyl ether to give 4-{2-[6-(4-tert-butylbenzenesulfonylamino )-5-(4-methylphenyl)pyrimidin-4-yloxy]ethoxy}phenoxyacetic acid (1.14 g).

Workup

  1. temperaturecooling
  2. washwashed with water
  3. extractionextracted with 10% aqueous sodium hydroxide solution
  4. washThe aqueous layer is washed with chloroform
  5. temperaturecooling
  6. extractionThe mixture is extracted with ethyl acetate
  7. washthe extract is washed
  8. customdried
  9. customevaporated
  10. customto remove the solvent
  11. customThe residue is crystallized from ethyl acetate/diisopropyl ether

Sources & evidence

ORD record
ord-14065763303a4ca68aa0bbb60db8d876
Source dataset
uspto-grants-1996_12
Patent number
US05589478

Linked notes

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