Potassium Hydroxide → (3-cyclopropyl-2-oxo-4-phenyl-2,3-dihydro-1H-imidazol-1-yl)-acetic acid
Reaction equation
C([O:3][C:4](=[O:21])[CH2:5][N:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:8]([CH:17]2[CH2:19][CH2:18]2)[C:7]1=[O:20])C.[OH-].[K+]>CO>[CH:17]1([N:8]2[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:10][N:6]([CH2:5][C:4]([OH:21])=[O:3])[C:7]2=[O:20])[CH2:19][CH2:18]1Participants
4
Procedure
350 mg (1.222 mmol) of ethyl (3-cyclopropyl-2-oxo-4-phenyl-2,3-dihydro-1H-imidazol-1-yl)-acetate from Example 123A are placed in 2 ml methanol, treated with 0.5 ml 20% aqueous potassium hydroxide and stirred for two hours at room temperature. The methanol is removed on the rotary evaporator, and the residue acidified with 2 N hydrochloric acid and extracted with dichloromethane. The organic phase is separated, dried over sodium sulphate and concentrated. It is purified by flash chromatography on silica gel (eluent: dichloromethane/methanol first 50:1, then 25:1). 166 mg (53% of theory) of the target compound are thus obtained.