Ethanol → 3-[[2-Fluoro-5-[3-(hydroxymethyl)-1-piperidyl]benzoyl]amino]-2,4-dimethyl-benzoic acid

HRID 239931Notes

Reaction equation

HRID 239931 reaction equation
[OH-].[Na+].[F:3][C:4]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:30][CH2:29][CH2:28][CH:27]([CH2:31][OH:32])[CH2:26]2)=[CH:21][C:5]=1[C:6]([NH:8][C:9]1[C:10]([CH3:20])=[C:11]([CH:16]=[CH:17][C:18]=1[CH3:19])[C:12]([O:14]C)=[O:13])=[O:7].CCO>O.C1COCC1>[F:3][C:4]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:30][CH2:29][CH2:28][CH:27]([CH2:31][OH:32])[CH2:26]2)=[CH:21][C:5]=1[C:6]([NH:8][C:9]1[C:10]([CH3:20])=[C:11]([CH:16]=[CH:17][C:18]=1[CH3:19])[C:12]([OH:14])=[O:13])=[O:7]

Participants

6

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 86707317Methyl 3-[[2-fluoro-5-[3-(hydroxymethyl)-1-piperidyl]benzoyl]amino]-2,4-dimethyl-benzoate

Product 1

HCID 867073183-[[2-Fluoro-5-[3-(hydroxymethyl)-1-piperidyl]benzoyl]amino]-2,4-dimethyl-benzoic acidYield 36.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of NaOH (0.146 mg, 0.00366 mol) in 1.5 ml of H2O is added to a stirred solution of methyl 3-[[2-fluoro-5-[3-(hydroxymethyl)-1-piperidyl]benzoyl]amino]-2,4-dimethyl-benzoate (0.38 g, 0.000916 mol) in THF:EtOH (3 ml:2 ml). After 4 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 ethyl acetate. The organic layer are combined and dried over anhydrous sodium sulfate. The solvent is removed under reduced pressure to afford the title compound as a light yellow solid (85 mg g, 36.8%). Mass spectrum (m/z): 401.2 (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

Sources & evidence

ORD record
ord-94f070f1972845448fdf4d667aec139f
Source dataset
uspto-grants-2014_02
Patent number
US08642768B2

Reaction notes

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