Sodium Hydroxide → (Butyl((4-methylphenyl)sulfonyl)amino)acetic acid

HRID 1647697Notes

Reaction equation

HRID 1647697 reaction equation
C([O:3][C:4](=[O:21])[CH2:5][N:6]([CH2:17][CH2:18][CH2:19][CH3:20])[S:7]([C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1)(=[O:9])=[O:8])C.[OH-].[Na+]>CO.O>[CH2:17]([N:6]([CH2:5][C:4]([OH:21])=[O:3])[S:7]([C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1)(=[O:9])=[O:8])[CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 131719040HCID 131719040, compound

Product 1

HCID 4177985(Butyl((4-methylphenyl)sulfonyl)amino)acetic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

Dissolve the crude ethyl-[butyl-(toluene-4-sulfonyl)-amino]-acetate (10 mmol) in methanol (25 mL) and water (25 mL). Add sodium hydroxide (10 mmol) and stir the reaction at room temperature for 5 hours. Dilute the reaction with water (100 mL) and rinse with methylene chloride. Neutralize the aqueous with 1N hydrochloric acid and extract with methylene chloride (3×75 mL). Combine the organic extracts and rinse with water (100 mL), brine (100 mL), dry over anhydrous sodium sulfate, filter and concentrate under vacuum to provide [butyl-(toluene-4-sulfonyl)-amino]-acetic acid.

Workup

  1. customthe reaction at room temperature for 5 hours
  2. additionDilute
  3. washrinse with methylene chloride
  4. extractionextract with methylene chloride (3×75 mL)
  5. washCombine the organic extracts and rinse with water (100 mL), brine (100 mL)
  6. dry with materialdry over anhydrous sodium sulfate
  7. filtrationfilter
  8. concentrationconcentrate under vacuum

Sources & evidence

ORD record
ord-68996f71e092425ca4d494cb82340f3b
Source dataset
uspto-grants-1995_07
Patent number
US05434145

Reaction notes

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