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

HRID 1428717Notes

Reaction equation

HRID 1428717 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].[OH-].[Li+]>O1CCCC1.O>[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

4

Reactant 2

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

Product 1

HCID 866793652-(3-Fluoro-4-(methylsulfonamidomethyl)phenyl)propanoic acidYield 86%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

The ethyl 2-(3-fluoro-4-(methylsulfonamidomethyl)phenyl)propanoate (12.5 g, 40.4 mmol) was dissolved in tetrahydrofuran-water mixture (120 mL, 2:1), lithium hydroxide (2.8 g, 121.1 mmol) was added and refluxing carried out for 12 h. After evaporation of the organic solvent under reduced pressure, the reaction mixture was extracted with diethyl ether (2×100 mL). The aqueous layer was acidified using 1 N HCl solution to pH=2 and extracted with dichloromethane (3×250 mL). The combined organic layer was dried over magnesium sulfate and concentrated under reduced pressure to afford 2-(3-fluoro-4-(methylsulfonamido-methyl)phenyl)propanoic acid (9.56 g, 86%).

Workup

  1. temperaturerefluxing
  2. customAfter evaporation of the organic solvent under reduced pressure
  3. extractionthe reaction mixture was extracted with diethyl ether (2×100 mL)
  4. extractionextracted with dichloromethane (3×250 mL)
  5. dry with materialThe combined organic layer was dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a0d9de1206574de3ba663138fbe9ff4a
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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