2-(4-Methoxy-benzenesulfonyl)-3-phenyl-propionic acid ethyl ester → 2-(4-Methoxy-benzenesulfonyl)3-phenyl-propionic acid

HRID 565284Notes

Reaction equation

HRID 565284 reaction equation
C([O:3][C:4](=[O:24])[CH:5]([S:13]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)(=[O:15])=[O:14])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)C>CO.[OH-].[Na+]>[CH3:23][O:22][C:19]1[CH:18]=[CH:17][C:16]([S:13]([CH:5]([CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:4]([OH:24])=[O:3])(=[O:15])=[O:14])=[CH:21][CH:20]=1

Participants

4

Reactant 1

HCID 108934292-(4-Methoxy-benzenesulfonyl)-3-phenyl-propionic acid ethyl ester

Product 1

HCID 108709182-(4-Methoxy-benzenesulfonyl)3-phenyl-propionic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a stirred solution of 2-(4-methoxy-benzenesulfonyl)-3-phenyl-propionic acid ethyl ester (348 mg, 1 mmol) in methanol (25 ml), 10 N NaOH (10 ml) was added. The reaction mixture was stirred at room temperature for 48 hours. At the end, the reaction mixture was concentrated and carefully neutralized with dilute HCl. The residue obtained was extracted with chloroform, washed well with water, dried and concentrated. The product obtained was purified by silica-gel column chromatography by eluting with ethyl acetate: methanol (95:5) to afford 2-(4-methoxy-benzenesulfonyl)-3-phenyl-propionic acid as a colorless oil. Yield: 250 mg, 89%; MS: 321 (M+H)+.

Workup

  1. concentrationAt the end, the reaction mixture was concentrated
  2. customThe residue obtained
  3. extractionwas extracted with chloroform
  4. washwashed well with water
  5. customdried
  6. concentrationconcentrated
  7. customThe product obtained
  8. customwas purified by silica-gel column chromatography
  9. washby eluting with ethyl acetate: methanol (95:5)

Sources & evidence

ORD record
ord-d8e31223ef394304ace3546533794716
Source dataset
uspto-grants-2001_01
Patent number
US06172057B2

Reaction notes

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