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

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

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.