Water → 2-(3-Fluoro-4-(methylsulfonamidomethyl)phenyl)propanoic acid

HRID 1428728Notes

Reaction equation

HRID 1428728 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:14]([CH3:20])[C:15]([O:17]CC)=[O:16])[CH:5]=[CH:6][C:7]=1[CH2:8][NH:9][S:10]([CH3:13])(=[O:12])=[O:11].O1CCCC1.O.[OH-].[Li+]>C(OCC)(=O)C.C(O)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:14]([CH3:20])[C:15]([OH:17])=[O:16])[CH:5]=[CH:6][C:7]=1[CH2:8][NH:9][S:10]([CH3:13])(=[O:11])=[O:12]

Participants

7

Reactant 4

HCID 962WaterHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 70855559Ethyl 2-(3-fluoro-4-(methylsulfonamidomethyl)phenyl)propanoate

Product 1

HCID 866793652-(3-Fluoro-4-(methylsulfonamidomethyl)phenyl)propanoic acidYield 52.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of ethyl 2-(3-fluoro-4-(methylsulfonamidomethyl)phenyl)-propanoate (458 mg, 1.51 mmol) in co-solvent with tetrahydrofuran and water (1:1) were added lithium hydroxide (190 mg, 4.529 mmol). The reaction mixture was refluxed for 15 h, then cooled to room temperature, acidified to pH 3-4 with acetic acid. The residue dissolved in ethyl acetate and washed with water and brine. The organic layer was dried over magnesium sulfate and filtered. The filtrate was removed in vacuo. The crude was purified by column chromatography to give 2-(3-fluoro-4-(methylsulfonamidomethyl)phenyl)propanoic acid (218 mg, 52%).

Workup

  1. temperatureThe reaction mixture was refluxed for 15 h
  2. washwashed with water and brine
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. customThe filtrate was removed in vacuo
  6. customThe crude was purified by column chromatography

Sources & evidence

ORD record
ord-d4568d27853c40ad9b37d7d6315a4215
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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