Lithium Hydroxide → 4-Methyl-2-[pyridine-3-carbonyl]-amino-pentanoic acid

HRID 82498Notes

Reaction equation

HRID 82498 reaction equation
C[O:2][C:3](=[O:18])[C:4]([NH2:17])([C:9]([C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)=[O:10])[CH2:5][CH:6]([CH3:8])[CH3:7].C1COCC1.[Li+].[OH-]>CO.O>[CH3:7][CH:6]([CH3:8])[CH2:5][C:4]([NH2:17])([C:9]([C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)=[O:10])[C:3]([OH:18])=[O:2]

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 8028Tetrahydrofuran2×HCID 67325240HCID 67325240, compound

Product 1

HCID 673256494-Methyl-2-[pyridine-3-carbonyl]-amino-pentanoic acidYield 60%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 4-methyl-2-[pyridine-3-carbonyl]-amino-pentanoic acid methyl ester (0.80 g, 3.3 mmol), in methanol (8 mL), THF (3 mL) was added LiOH (0.7 g, 16.9 mmol), dissolved in water (9 mL). The mixture was allowed to stir at room temperature (25° C.) over 2.5 h. Methanol and THF was stripped off from the reaction mass, acidified the reaction mass using 1.5NHCl (pH=1). Extracted the reaction mass with ethyl acetate (100 mL) thrice and dried over sodium sulphate and concentrated to obtain product as pale yellow solid (0.45 g, 60%).

Workup

  1. extractionExtracted the reaction mass with ethyl acetate (100 mL) thrice
  2. dry with materialdried over sodium sulphate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-ecb67ae1468d4f908c766e03ad58f2d8
Source dataset
uspto-grants-2014_09
Patent number
US08846721B2

Reaction notes

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