Methanol → 2-(4-Cyclopropylsulfonylphenyl)-2-(2,4-difluoroanilino)acetic acid

HRID 524384Notes

Reaction equation

HRID 524384 reaction equation
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=3[F:27])[C:14]([O:16]CC)=[O:15])=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.[OH-].[Li+].C1COCC1.CO>O>[CH:1]1([S:4]([C:7]2[CH:8]=[CH:9][C:10]([CH:13]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=3[F:27])[C:14]([OH:16])=[O:15])=[CH:11][CH:12]=2)(=[O:5])=[O:6])[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 68182723Ethyl 2-(4-cyclopropylsulfonylphenyl)-2-(2,4-difluoroanilino)acetate

Product 1

HCID 681825192-(4-Cyclopropylsulfonylphenyl)-2-(2,4-difluoroanilino)acetic acidYield 90.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

To ethyl 2-(4-cyclopropylsulfonylphenyl)-2-(2,4-difluoroanilino)acetate (0.6 g, 1.51 mmol) was added a solution of lithium hydroxide (0.317 g, 7.22 mmol) in water (4 mL) followed by THF (4 mL) and methanol (0.5 mL) and stirred for 12 hours at 25° C. Organic solvents were evaporated from the reaction mixture and aqueous layer was acidified 1N HCl, extracted with ethyl acetate (3×15 mL), organic layer was washed with brine solution, dried over anhydrous sodium sulfate, and washed concentrated under reduced pressure to provide 2-(4-cyclopropylsulfonylphenyl)-2-(2,4-difluoroanilino)acetic acid (0.5 g).

Workup

  1. customOrganic solvents were evaporated from the reaction mixture and aqueous layer
  2. extractionextracted with ethyl acetate (3×15 mL), organic layer
  3. washwas washed with brine solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. washwashed
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8ea87a3a996b43d88cb0b55b9328bf0e
Source dataset
uspto-grants-2016_05
Patent number
US09340506B2

Reaction notes

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