Potassium Carbonate → 3-[2-[2-Chloro-4-(methylsulfonyl)phenoxy]-4-(trifluoromethyl)phenyl]propanoic acid

HRID 910832Notes

Reaction equation

HRID 910832 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[CH2:12][CH2:13][C:14]([O:16]C(C)(C)C)=[O:15].[CH3:21][S:22]([C:25]1[CH:30]=[CH:29][C:28](F)=[C:27]([Cl:32])[CH:26]=1)(=[O:24])=[O:23].C(=O)([O-])[O-].[K+].[K+]>CN1C(=O)CCC1>[Cl:32][C:27]1[CH:26]=[C:25]([S:22]([CH3:21])(=[O:24])=[O:23])[CH:30]=[CH:29][C:28]=1[O:1][C:2]1[CH:7]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:5]=[CH:4][C:3]=1[CH2:12][CH2:13][C:14]([OH:16])=[O:15]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 213408802-Chloro-1-fluoro-4-methylsulfonylbenzeneHCID 86620101tert-Butyl 3-[2-hydroxy-4-(trifluoromethyl)phenyl]propanoate

Product 1

HCID 116259773-[2-[2-Chloro-4-(methylsulfonyl)phenoxy]-4-(trifluoromethyl)phenyl]propanoic acid

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of the product from step (v) (0.6 g), the product from step (vii) (0.43 g) and potassium carbonate (0.285 g) in NMP (10 ml) was heated at 70° C. for 4 h. The mixture was partitioned between diethylether and water, the organic layer dried, and the solvent evaporated under reduced pressure. The residue was dissolved in 50% DCM/trifluoroacetic acid (20 ml) and stirred at RT for 2 h. The solvent was evaporated under reduced pressure and the residue purified by RPHPLC, yield 0.175 g

Workup

  1. customThe mixture was partitioned between diethylether and water
  2. customthe organic layer dried
  3. customthe solvent evaporated under reduced pressure
  4. dissolutionThe residue was dissolved in 50% DCM/trifluoroacetic acid (20 ml)
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue purified by RPHPLC, yield 0.175 g

Sources & evidence

ORD record
ord-a2ec5487dc8a4965a863958944d100c0
Source dataset
uspto-grants-2011_09
Patent number
US08022248B2

Reaction notes

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