Water → 2-(4-(Methylsulfonamidomethyl)phenyl)propanoic acid

HRID 1842984Notes

Reaction equation

HRID 1842984 reaction equation
[CH3:1][S:2]([NH:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]([CH3:19])[C:14]([O:16]CC)=[O:15])=[CH:9][CH:8]=1)(=[O:4])=[O:3].C1COCC1.O.[OH-].[Na+]>CCOC(C)=O.CC(O)=O>[CH3:1][S:2]([NH:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]([CH3:19])[C:14]([OH:16])=[O:15])=[CH:9][CH:8]=1)(=[O:4])=[O:3]

Participants

7

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 70816013Ethyl 2-(4-(methylsulfonamidomethyl)phenyl)propanoate

Product 1

HCID 708161912-(4-(Methylsulfonamidomethyl)phenyl)propanoic acidYield 25.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of ethyl 2-(4-(methylsulfonamidomethyl)phenyl)propanoate (325 mg, 1.139 mmol) in a co-solvent of THF and water (1:1) was added sodium hydroxide (114 mg, 2.8475 mmol). The reaction mixture was refluxed for 16 h, then cooled to room temperature, acidified to pH 3-4 with AcOH. The residue dissolved in EtOAc and washed with water and brine. The organic layer was dried (MgSO4) and filtered. The solvent removed in vacuo. The crude product was purified by CC. 2-(4-(methylsulfonamidomethyl)phenyl)propanoic acid (74 mg) was obtained in 25% yield.

Workup

  1. temperatureThe reaction mixture was refluxed for 16 h
  2. washwashed with water and brine
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. customThe solvent removed in vacuo
  6. customThe crude product was purified by CC

Sources & evidence

ORD record
ord-00b814f28b72468c8f9db7a3f8e4f311
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

Loading…