Methanol → 2,4-Dimethyl-3-[[2-methyl-5-(4-oxo-1-piperidyl)benzoyl]amino]benzoic acid

HRID 239954Notes

Reaction equation

HRID 239954 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[C:13]([NH:14][C:15](=[O:30])[C:16]2[CH:21]=[C:20]([N:22]3[CH2:27][CH2:26][C:25](=[O:28])[CH2:24][CH2:23]3)[CH:19]=[CH:18][C:17]=2[CH3:29])=[C:12]([CH3:31])[CH:11]=[CH:10][C:5]=1[C:6]([O:8]C)=[O:7].CO>C1COCC1>[CH3:3][C:4]1[C:13]([NH:14][C:15](=[O:30])[C:16]2[CH:21]=[C:20]([N:22]3[CH2:27][CH2:26][C:25](=[O:28])[CH2:24][CH2:23]3)[CH:19]=[CH:18][C:17]=2[CH3:29])=[C:12]([CH3:31])[CH:11]=[CH:10][C:5]=1[C:6]([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 86707338Methyl 2,4-dimethyl-3-[[2-methyl-5-(4-oxo-1-piperidyl)benzoyl]amino]benzoate

Product 1

HCID 867073402,4-Dimethyl-3-[[2-methyl-5-(4-oxo-1-piperidyl)benzoyl]amino]benzoic acidYield 50.12%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of aqueous 2N NaOH (1.00 ml) is added to a stirred solution of methyl 2,4-dimethyl-3-[[2-methyl-5-(4-oxo-1-piperidyl)benzoyl]amino]benzoate (0.12 g, 304.20 μmol) in THF:MeOH (2 ml:1 ml). After 16 hours at ambient temperature, the organic solvent is removed under reduced pressure and the residue is diluted with water, acidified to pH 6 with 1N HCl, and extracted with ethyl acetate. The organic layers are combined with aqueous layer and concentrated under reduced pressure. The resulting solids are dissolved in acetonitrile/H2O and lyophilized to afford the title compound as an off-white solid (58 mg, 50.12%). Mass spectrum (m/z): 381.2 (M+1).

Workup

  1. customthe organic solvent is removed under reduced pressure
  2. additionthe residue is diluted with water
  3. extractionextracted with ethyl acetate
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe resulting solids are dissolved in acetonitrile/H2O

Sources & evidence

ORD record
ord-80833518b8c7453da7b8dcc28f1dca57
Source dataset
uspto-grants-2014_02
Patent number
US08642768B2

Reaction notes

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