Hydrochloric Acid → HCID 59644596, compound

HRID 2252271Notes

Reaction equation

HRID 2252271 reaction equation
[CH3:1][O:2][C:3](=[O:23])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:13]=2[NH2:22])=[CH:7][CH:6]=1.[C:24](=O)([O-])[O-].[K+].[K+].[C:30]1(C)[C:31]([S:36](Cl)(=[O:38])=[O:37])=[CH:32][CH:33]=[CH:34][CH:35]=1.Cl>C(OCC)(=O)C.O>[CH3:1][O:2][C:3](=[O:23])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:20])([F:19])[F:21])=[CH:14][C:13]=2[NH:22][S:36]([C:31]2[CH:30]=[CH:35][C:34]([CH3:24])=[CH:33][CH:32]=2)(=[O:37])=[O:38])=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8623o-Toluenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 26189410Methyl 2-{4-[2-amino-4-(trifluoromethyl)phenoxy]-phenyl}acetate

Product 1

HCID 59644596HCID 59644596, compoundYield 37.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

[4-(2-Amino-4-trifluoromethyl-phenoxy)-phenyl]-acetic acid methyl ester (84 mg, 0.542 mmol) was added to a mixture of 150 mg (1.08 mmol) of potassium carbonate in 3 mL of ethyl acetate in presence of 0.5 mL of water. To the resulting mixture was added 155 mg (0.813 mmol) toluenesulfonyl chloride. The resulting mixture was allowed to stir at room temperature overnight. Upon completion, 20 mL of 2N HCl aqueous solution was added and the resulting mixture was extracted with ethyl acetate (3×30 mL). The combined extracts were washed with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was chromatographed to give 97 mg of {4-[2-(toluene-4-sulfonylamino)-4-trifluoromethyl-phenoxy]-phenyl}-acetic acid methyl ester. 1H NMR (CDCl3): δ 7.93 (s, 1H), 7.65 (d, J=8.36 Hz, 2H), 7.15-7.28 (m, 5H), 6.68 (d, J=8.68 Hz, 1H), 6.63 9d, J=8.48 Hz, 2H), 3.72 (s, 3H), 3.61 9s, 2H), 2.39 9s, 3H).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate (3×30 mL)
  2. washThe combined extracts were washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed

Sources & evidence

ORD record
ord-58b456e89b384732bb4a28f1f91f96ed
Source dataset
uspto-grants-2008_01
Patent number
US07321001B2

Reaction notes

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