Sodium Hydroxide → 3-[[6-[3-(Hydroxymethyl)-1-piperidyl]-3-methyl-pyridine-2-carbonyl]amino]-2,4-dimethyl-benzoic acid

HRID 239966Notes

Reaction equation

HRID 239966 reaction equation
[OH-].[Na+].[OH:3][CH2:4][CH:5]1[CH2:10][CH2:9][CH2:8][N:7]([C:11]2[N:16]=[C:15]([C:17]([NH:19][C:20]3[C:21]([CH3:31])=[C:22]([CH:27]=[CH:28][C:29]=3[CH3:30])[C:23]([O:25]C)=[O:24])=[O:18])[C:14]([CH3:32])=[CH:13][CH:12]=2)[CH2:6]1>C1COCC1>[OH:3][CH2:4][CH:5]1[CH2:10][CH2:9][CH2:8][N:7]([C:11]2[N:16]=[C:15]([C:17]([NH:19][C:20]3[C:21]([CH3:31])=[C:22]([CH:27]=[CH:28][C:29]=3[CH3:30])[C:23]([OH:25])=[O:24])=[O:18])[C:14]([CH3:32])=[CH:13][CH:12]=2)[CH2:6]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86707349Methyl 3-[[6-[3-(hydroxymethyl)-1-piperidyl]-3-methyl-pyridine-2-carbonyl]amino]-2,4-dimethyl-benzoate

Product 1

HCID 867073503-[[6-[3-(Hydroxymethyl)-1-piperidyl]-3-methyl-pyridine-2-carbonyl]amino]-2,4-dimethyl-benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of aqueous 2N NaOH (3.00 ml) is added to a stirred solution of methyl 3-[[6-[3-(hydroxymethyl)-1-piperidyl]-3-methyl-pyridine-2-carbonyl]amino]-2,4-dimethyl-benzoate (0.18 g, 0.437 mmol) in THF (8 ml). After 12 hours at ambient temperature, the organic solvent is removed under reduced pressure and the residue is diluted with water, acidified to pH 4 with citric acid, and extracted with ethyl acetate. The organic layers are combined and dried over anhydrous sodium sulfate. The solvent is removed under reduced pressure and the resulting residue is purified by preparative HPLC to afford the title compound as off white solid (57 mg, 14%). Mass spectrum (m/z): 398.2 (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. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent is removed under reduced pressure
  6. customthe resulting residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-00503d96c6d74dc6b121e4932070d177
Source dataset
uspto-grants-2014_02
Patent number
US08642768B2

Reaction notes

Loading…