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

HRID 239939Notes

Reaction equation

HRID 239939 reaction equation
[OH-].[Na+].[OH:3][CH2:4][CH:5]1[CH2:10][CH2:9][CH2:8][N:7]([C:11]2[CH:12]=[CH:13][C:14]([CH3:32])=[C:15]([CH:31]=2)[C:16]([NH:18][C:19]2[C:28]([CH3:29])=[CH:27][C:22]([C:23]([O:25]C)=[O:24])=[CH:21][C:20]=2[CH3:30])=[O:17])[CH2:6]1.CO>C1COCC1>[OH:3][CH2:4][CH:5]1[CH2:10][CH2:9][CH2:8][N:7]([C:11]2[CH:12]=[CH:13][C:14]([CH3:32])=[C:15]([CH:31]=2)[C:16]([NH:18][C:19]2[C:20]([CH3:30])=[CH:21][C:22]([C:23]([OH:25])=[O:24])=[CH:27][C:28]=2[CH3:29])=[O:17])[CH2:6]1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 86707325Methyl 4-[[5-[3-(hydroxymethyl)-1-piperidyl]-2-methyl-benzoyl]amino]-3,5-dimethyl-benzoate

Product 1

HCID 867073264-[[5-[3-(Hydroxymethyl)-1-piperidyl]-2-methyl-benzoyl]amino]-3,5-dimethyl-benzoic acidYield 93.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of aqueous 4N NaOH (2.00 ml) is added to a stirred solution of methyl 4-[[5-[3-(hydroxymethyl)-1-piperidyl]-2-methyl-benzoyl]amino]-3,5-dimethyl-benzoate (0.3 g, 0.73 mmol) in THF:MeOH (10 ml:5 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 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 a light brown solid (0.27 g, 90%). Mass spectrum (m/z): 397.2 (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-64e7b9a6132e49d59fbb2e16bff9d935
Source dataset
uspto-grants-2014_02
Patent number
US08642768B2

Reaction notes

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