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

HRID 1427100Notes

Reaction equation

HRID 1427100 reaction equation
[OH-].[Na+].[OH:3][CH:4]1[CH2:9][CH2:8][CH2:7][N:6]([C:10]2[CH:11]=[CH:12][C:13]([CH3:31])=[C:14]([CH:30]=2)[C:15]([NH:17][C:18]2[C:19]([CH3:29])=[C:20]([CH:25]=[CH:26][C:27]=2[CH3:28])[C:21]([O:23]C)=[O:22])=[O:16])[CH2:5]1.CO>C1COCC1>[OH:3][CH:4]1[CH2:9][CH2:8][CH2:7][N:6]([C:10]2[CH:11]=[CH:12][C:13]([CH3:31])=[C:14]([CH:30]=2)[C:15]([NH:17][C:18]2[C:19]([CH3:29])=[C:20]([CH:25]=[CH:26][C:27]=2[CH3:28])[C:21]([OH:23])=[O:22])=[O:16])[CH2:5]1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 86707331Methyl 3-[[5-(3-hydroxy-1-piperidyl)-2-methyl-benzoyl]amino]-2,4-dimethyl-benzoate

Product 1

HCID 867073323-[[5-(3-Hydroxy-1-piperidyl)-2-methyl-benzoyl]amino]-2,4-dimethyl-benzoic acidYield 95.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of aqueous 4N NaOH (2.00 ml) is added to a stirred solution of methyl 3-[[5-(3-hydroxy-1-piperidyl)-2-methyl-benzoyl]amino]-2,4-dimethyl-benzoate (0.3 g, 0.75 mmol) in THF:MeOH (5 ml:2 ml). After 3 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 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 an off-white solid (0.274 g, 94%). Mass spectrum (m/z): 383.2 (M+1).

Workup

  1. customthe organic solvent is removed under reduced pressure
  2. additionthe residue is diluted with water
  3. extractionextracted with 10% IPA in CH2Cl2
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent is removed under reduced pressure
  6. customthe resulting precipitate is triturated with diethyl ether
  7. filtrationfiltered

Sources & evidence

ORD record
ord-f872883745744520ac46439bd177cc81
Source dataset
uspto-grants-2015_01
Patent number
US08933098B2

Reaction notes

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