Hydrochloric Acid → HCID 59644644, compound

HRID 2252272Notes

Reaction equation

HRID 2252272 reaction equation
C[O:2][C:3](=[O:33])[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[NH:22][S:23]([C:26]2[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=2)(=[O:25])=[O:24])=[CH:7][CH:6]=1.[OH-].[Li+].Cl>CO.O>[C:29]1([CH3:32])[CH:28]=[CH:27][C:26]([S:23]([NH:22][C:13]2[CH:14]=[C:15]([C:18]([F:21])([F:19])[F:20])[CH:16]=[CH:17][C:12]=2[O:11][C:8]2[CH:7]=[CH:6][C:5]([CH2:4][C:3]([OH:33])=[O:2])=[CH:10][CH:9]=2)(=[O:24])=[O:25])=[CH:31][CH:30]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59644596HCID 59644596, compound

Product 1

HCID 59644644HCID 59644644, compoundYield 74.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of {4-[2-(toluene-4-sulfonylamino)-4-trifluoromethyl-phenoxy]-phenyl}-acetic acid methyl ester (97 mg, 0.202 mmol) in 1 mL of methanol was added 1 mL of a suspension of lithium hydroxide (42 mg, 1.01 mmol) in 1 mL of water. The resulting mixture was allowed to stir at room temperature until all starting material disappeared. Upon completion, 50 mL of 1N aqueous HCl was added and the resulting mixture was extracted with ethyl acetate (3×30 mL). The combined extracts were washed with 1N HCl aqueous solution (20 mL), water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography to give 70 mg of {4-[2-(toluene-4-sulfonyl-amino)-4-trifluoromethyl-phenoxy]-phenyl}-acetic acid (1). 1H NMR (CD3OD): δ 7.84 (d, J=1.92 Hz, 1H), 7.58 (d, J=8.27, 1.6 Hz, 2H), 7.32 (dd, J=8.27, 1.6 Hz, 1H), 7.18-7.30 (m, 5H), 6.73 (d, J=8.53 Hz, 1H), 6.57 (d, J=8.53 Hz, 2H), 3.59 (s, 2H), 2.37 (s, 3H). LCMS (ESI−) 464 (M−1).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate (3×30 mL)
  2. washThe combined extracts were washed with 1N HCl aqueous solution (20 mL), water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-58563ec86e9d4c59bf0341ed969e6c20
Source dataset
uspto-grants-2008_01
Patent number
US07321001B2

Reaction notes

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