Methanol → 4-[[6-(4-Hydroxy-4-methyl-1-piperidyl)-3-methyl-pyridine-2-carbonyl]amino]-3,5-dimethyl-benzoic acid

HRID 239969Notes

Reaction equation

HRID 239969 reaction equation
[OH-].[Na+].[OH:3][C:4]1([CH3:33])[CH2:9][CH2:8][N:7]([C:10]2[N:15]=[C:14]([C:16]([NH:18][C:19]3[C:29]([CH3:30])=[CH:28][C:22]([C:23]([O:25]CC)=[O:24])=[CH:21][C:20]=3[CH3:31])=[O:17])[C:13]([CH3:32])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1.CO>C1COCC1>[OH:3][C:4]1([CH3:33])[CH2:5][CH2:6][N:7]([C:10]2[N:15]=[C:14]([C:16]([NH:18][C:19]3[C:20]([CH3:31])=[CH:21][C:22]([C:23]([OH:25])=[O:24])=[CH:28][C:29]=3[CH3:30])=[O:17])[C:13]([CH3:32])=[CH:12][CH:11]=2)[CH2:8][CH2:9]1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 86707351Ethyl 4-[[6-(4-Hydroxy-4-Methyl-1-Piperidyl)-3-Methyl-Pyridine-2-carbonyl]amino]-3,5-dimethyl-benzoate

Product 1

HCID 867073524-[[6-(4-Hydroxy-4-methyl-1-piperidyl)-3-methyl-pyridine-2-carbonyl]amino]-3,5-dimethyl-benzoic acidYield 43.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of aqueous 2N NaOH (5.00 ml) is added to a stirred solution of ethyl 4-[[6-(4-hydroxy-4-methyl-1-piperidyl)-3-methyl-pyridine-2-carbonyl]amino]-3,5-dimethyl-benzoate (0.27 g, 634.51 mmol) in THF:MeOH (10 ml:5 ml). After 1 hour at 50° C., the organic solvent is removed under reduced pressure and the residue is diluted with water, acidified to pH 6 with 5N HCl, and extracted with ethyl acetate. The organic layers are combined with aqueous layer and concentrated under reduced pressure. The solids are triturated with acetone/acetonitrile and filtered. The filtrate is dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford the title compound as an off-white solid (0.11 g, 43.6%). 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. concentrationconcentrated under reduced pressure
  5. customThe solids are triturated with acetone/acetonitrile
  6. filtrationfiltered
  7. dry with materialThe filtrate is dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-430e387b0fe24c12952ede0f672269d2
Source dataset
uspto-grants-2014_02
Patent number
US08642768B2

Reaction notes

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