Ethyl 3-ethyl-6-(4-fluorobenzenesulphonylmethyl)-2-methoxybenzoate → 3-Ethyl-6-(4-fluorobenzenesulphonyl-methyl)-2-methoxybenzoic acid

HRID 2177672Notes

Reaction equation

HRID 2177672 reaction equation
[CH2:1]([C:3]1[C:4]([O:25][CH3:26])=[C:5]([C:11]([CH2:14][S:15]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)(=[O:17])=[O:16])=[CH:12][CH:13]=1)[C:6]([O:8]CC)=[O:7])[CH3:2]>C1COCC1.O>[CH2:1]([C:3]1[C:4]([O:25][CH3:26])=[C:5]([C:11]([CH2:14][S:15]([C:18]2[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=2)(=[O:17])=[O:16])=[CH:12][CH:13]=1)[C:6]([OH:8])=[O:7])[CH3:2]

Participants

4

Reactant 1

HCID 67108051Ethyl 3-ethyl-6-(4-fluorobenzenesulphonylmethyl)-2-methoxybenzoate2×

Product 1

HCID 529142903-Ethyl-6-(4-fluorobenzenesulphonyl-methyl)-2-methoxybenzoic acidYield 19.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Potassium trimethylsilanoate (0.257 g) was added to a solution of ethyl 3-ethyl-6-(4-fluorobenzenesulphonylmethyl)-2-methoxybenzoate (Intermediate 23, 0.076 g) in dry THF (10 ml). The resultant mixture was stirred at room temperature for 3 days. The mixture was diluted with water and washed with ethyl acetate. The aqueous layer was acidified by careful addition of concentrated hydrochloric acid and then extracted with ethyl acetate, washed with water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by preparative HPLC (C18), eluting with a mixture of methanol and water containing 0.1% formic acid with a gradient of 50-80% to give 3-ethyl-6-(4-fluorobenzenesulphonyl-methyl)-2-methoxybenzoic acid (0.014 g) as a white solid.

Workup

  1. washwashed with ethyl acetate
  2. additionThe aqueous layer was acidified by careful addition of concentrated hydrochloric acid
  3. extractionextracted with ethyl acetate
  4. washwashed with water
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness
  8. customthe residue was purified by preparative HPLC (C18)
  9. washeluting with a mixture of methanol and water containing 0.1% formic acid with a gradient of 50-80%

Sources & evidence

ORD record
ord-8ea893d8768c48c4bcad1f5934d96009
Source dataset
uspto-grants-2015_06
Patent number
US09067905B2

Reaction notes

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