Sodium Hydroxide → (4-(2-Benzoxazolyl)amino-5-chloro-2-fluorophenyl)acetic acid
Reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]1[C:16]([Cl:17])=[CH:15][C:14]([CH2:18][C:19]([O:21]CC)=[O:20])=[C:13]([F:24])[CH:12]=1.[OH-].[Na+]>C1COCC1>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]1[C:16]([Cl:17])=[CH:15][C:14]([CH2:18][C:19]([OH:21])=[O:20])=[C:13]([F:24])[CH:12]=1Participants
4
Procedure
Ethyl (4-(2-benzoxazolyl)amino-5-chloro-2-fluorophenyl)acetate (570 mg, 1.63 mmol) was dissolved in THF (5 ml). To the resulting solution was added 1N NaOH (5.0 ml, 5.00 mmol), followed by stirring at room temperature for 20 hours. The reaction mixture was poured in ice-1N HCl to acidify therewith. The crystals thus precipitated were collected by filtration under reduced pressure, washed with water and dried under reduced pressure to give (4-(2-benzoxazolyl)amino-5-chloro-2-fluorophenyl)acetic acid (497 mg, 95%) as a brown solid.