Sodium Hydroxide → 3-[[6-[3-(Hydroxymethyl)-1-piperidyl]-3-methyl-pyridine-2-carbonyl]amino]-2,4-dimethyl-benzoic acid
Reaction equation
[OH-].[Na+].[OH:3][CH2:4][CH:5]1[CH2:10][CH2:9][CH2:8][N:7]([C:11]2[N:16]=[C:15]([C:17]([NH:19][C:20]3[C:21]([CH3:31])=[C:22]([CH:27]=[CH:28][C:29]=3[CH3:30])[C:23]([O:25]C)=[O:24])=[O:18])[C:14]([CH3:32])=[CH:13][CH:12]=2)[CH2:6]1>C1COCC1>[OH:3][CH2:4][CH:5]1[CH2:10][CH2:9][CH2:8][N:7]([C:11]2[N:16]=[C:15]([C:17]([NH:19][C:20]3[C:21]([CH3:31])=[C:22]([CH:27]=[CH:28][C:29]=3[CH3:30])[C:23]([OH:25])=[O:24])=[O:18])[C:14]([CH3:32])=[CH:13][CH:12]=2)[CH2:6]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of aqueous 2N NaOH (3.00 ml) is added to a stirred solution of methyl 3-[[6-[3-(hydroxymethyl)-1-piperidyl]-3-methyl-pyridine-2-carbonyl]amino]-2,4-dimethyl-benzoate (0.18 g, 0.437 mmol) in THF (8 ml). After 12 hours at ambient temperature, the organic solvent is removed under reduced pressure and the residue is diluted with water, acidified to pH 4 with citric acid, and extracted with ethyl acetate. The organic layers are combined and dried over anhydrous sodium sulfate. The solvent is removed under reduced pressure and the resulting residue is purified by preparative HPLC to afford the title compound as off white solid (57 mg, 14%). Mass spectrum (m/z): 398.2 (M+1).