Hydrochloric Acid → 3-Methyl-2-[pyridine-3-carbonyl-amino]-pentanoic acid
Reaction equation
C[O:2][C:3](=[O:18])[CH:4]([NH:9][C:10]([C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)=[O:11])[CH:5]([CH3:8])[CH2:6][CH3:7].C1COCC1.[Li+].[OH-].Cl>CO.O>[CH3:8][CH:5]([CH2:6][CH3:7])[CH:4]([NH:9][C:10]([C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)=[O:11])[C:3]([OH:18])=[O:2]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 25 °C
Procedure
To a solution of 3-methyl-2-[pyridine-3-carbonyl-amino]-pentanoic acid methyl ester (1.5 g, 5.9 mmol), in methanol (10 mL), THF (9 mL), was added LiOH (1.25 g, 29.9 mmol) dissolved in water (3 mL). The mixture was allowed to stir at room temperature (25° C.) over 3 h. Methanol and THF was stripped off from the reaction mass, acidified the reaction mass using 1.5N HCl (pH=2-3). Extracted the reaction mass with ethyl acetate (100 mL) thrice and dried over sodium sulphate and concentrated to obtain product as pale yellow solid (0.7 g, 50%).
Workup
- extractionExtracted the reaction mass with ethyl acetate (100 mL) thrice
- dry with materialdried over sodium sulphate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-7d62649520f64d96b695ecfb33956a17
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846721B2
Reaction notes
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