Sodium Hydroxide → 3-[[5-[3-(Hydroxymethyl)pyrrolidin-1-yl]-2-methyl-benzoyl]amino]-2,4-dimethyl-benzoic acid
Reaction equation
[OH-].[Na+].[OH:3][CH2:4][CH:5]1[CH2:10]C[CH2:8][N:7]([C:11]2[CH:12]=[CH:13][C:14]([CH3:32])=[C:15]([CH:31]=2)[C:16]([NH:18][C:19]2[C:20]([CH3:30])=[C:21]([CH:26]=[CH:27][C:28]=2[CH3:29])[C:22]([O:24]C)=[O:23])=[O:17])[CH2:6]1>CO>[OH:3][CH2:4][CH:5]1[CH2:10][CH2:8][N:7]([C:11]2[CH:12]=[CH:13][C:14]([CH3:32])=[C:15]([CH:31]=2)[C:16]([NH:18][C:19]2[C:20]([CH3:30])=[C:21]([CH:26]=[CH:27][C:28]=2[CH3:29])[C:22]([OH:24])=[O:23])=[O:17])[CH2:6]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of aqueous 5N NaOH (5.00 ml) is added to a stirred solution of methyl 3-[[5-[3-(hydroxymethyl)-1-piperidyl]-2-methyl-benzoyl]amino]-2,4-dimethyl-benzoate (0.4 g, 0.975 mmol) in MeOH (5 ml). After 5 hours at ambient temperature, the organic solvent is removed under reduced pressure and the residue is diluted with water, acidified to pH 4 with 1N HCl, and extracted twice with 10% IPA in CH2Cl2. The organic layers are combined and dried over anhydrous sodium sulfate. The solvent is removed under reduced pressure and the resulting precipitate is triturated with diethyl ether and filtered to afford the title compound as a brown solid (70 mg, 56%). Mass spectrum (m/z): 381.2 (M−1).