Hydrochloric Acid → 3-Methyl-2-[pyridine-3-carbonyl-amino]-pentanoic acid

HRID 82481

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

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
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846721B2

Linked notes

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