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

HRID 239949Notes

Reaction equation

HRID 239949 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[CH:5]=[C:6]([CH:12]=[C:13]([CH3:32])[C:14]=1[NH:15][C:16](=[O:31])[C:17]1[CH:22]=[C:21]([N:23]2[CH2:28][CH2:27][C:26](=[O:29])[CH2:25][CH2:24]2)[CH:20]=[CH:19][C:18]=1[CH3:30])[C:7]([O:9]CC)=[O:8].CO>C1COCC1>[CH3:32][C:13]1[CH:12]=[C:6]([CH:5]=[C:4]([CH3:3])[C:14]=1[NH:15][C:16](=[O:31])[C:17]1[CH:22]=[C:21]([N:23]2[CH2:24][CH2:25][C:26](=[O:29])[CH2:27][CH2:28]2)[CH:20]=[CH:19][C:18]=1[CH3:30])[C:7]([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 86707335Ethyl 3,5-dimethyl-4-[[2-methyl-5-(4-oxo-1-piperidyl)benzoyl]amino]benzoate

Product 1

HCID 867073363,5-Dimethyl-4-[[2-methyl-5-(4-oxo-1-piperidyl)benzoyl]amino]benzoic acidYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of aqueous 2N NaOH (2.00 ml) is added to a stirred solution of ethyl 3,5-dimethyl-4-[[2-methyl-5-(4-oxo-1-piperidyl)benzoyl]amino]benzoate (0.11 g, 269.28 μmol) in THF:MeOH (2.4 ml:1.2 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 7 with 1N HCl, and extracted twice with ethyl acetate. The organic layers are combined with aqueous layer and concentrated under reduced pressure. The resulting solids are triturated with 1:1 mixture of acetonitrile and ethanol to give white slurry that is filtered through Celite™ bed. The filtrate is concentrated under reduced pressure and the precipitate is triturated with acetone and filtered to afford the title compound as an off-white solid (99 mg, 99%). 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 twice with ethyl acetate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting solids are triturated with 1:1 mixture of acetonitrile and ethanol
  6. customto give white slurry that
  7. filtrationis filtered through Celite™ bed
  8. concentrationThe filtrate is concentrated under reduced pressure
  9. customthe precipitate is triturated with acetone
  10. filtrationfiltered

Sources & evidence

ORD record
ord-c748a1a556c5433c963d51b12d8436b8
Source dataset
uspto-grants-2014_02
Patent number
US08642768B2

Reaction notes

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