Lithium Hydroxide → 4-((3-Pyridinylcarbonyl)amino)butanoic acid

HRID 82496Notes

Reaction equation

HRID 82496 reaction equation
C[O:2][C:3](=[O:16])[CH2:4][CH2:5][CH2:6][NH:7][C:8]([C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)=[O:9].[Li+].[OH-].C(Cl)(Cl)Cl>C1COCC1.O>[N:12]1[CH:13]=[CH:14][CH:15]=[C:10]([C:8]([NH:7][CH2:6][CH2:5][CH2:4][C:3]([OH:16])=[O:2])=[O:9])[CH:11]=1

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 6212ChloroformHCID 40046204[(Pyridine-3-carbonyl)-amino]-butyric acid methyl ester

Product 1

HCID 606084-((3-Pyridinylcarbonyl)amino)butanoic acidYield 82.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 4[(pyridine-3-carbonyl)-amino]-butyric acid methyl ester (0.8 g, 3.5 mmol), in THF (14 mL) was added LiOH (0.75 g, 17.9 mmol), dissolved in water (6 mL). The mixture was allowed to stir at room temperature (25° C.) overnight. 50% starting material remains as such. Then reaction mixture heated at (45° C.). The reaction did not progress. The reaction mixture was worked up with chloroform to recover the starting material. The aqueous layer was diluted with water, acidified with 1.5N HCl till (pH=2-3), extracted with ethyl acetate (150 mL) and dried over sodium sulphate, concentrated to obtain yellow colour solid (0.6 g, 80%).

Workup

  1. customThen reaction mixture
  2. temperatureheated at (45° C.)
  3. customto recover the starting material
  4. additionThe aqueous layer was diluted with water
  5. extractionextracted with ethyl acetate (150 mL)
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a00a39158e1f4a21b98e9c3f22a67003
Source dataset
uspto-grants-2014_09
Patent number
US08846721B2

Reaction notes

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