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

HRID 1427108Notes

Reaction equation

HRID 1427108 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-ae081c9bf3c648aaab93b03426b579eb
Source dataset
uspto-grants-2015_01
Patent number
US08933098B2

Reaction notes

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