Lithium Hydroxide → 3-Phenyl-2-((pyridin-3-yl)formamido)propanoic acid

HRID 82475Notes

Reaction equation

HRID 82475 reaction equation
C[O:2][C:3](=[O:21])[CH:4]([NH:12][C:13]([C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Li+].[OH-]>CO.C1COCC1.O>[C:6]1([CH2:5][CH:4]([NH:12][C:13]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[O:14])[C:3]([OH:21])=[O:2])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 699200023-Phenyl-2-[(pyridine-3-carbonyl)-amino]-propionic acid methylester

Product 1

HCID 3365543-Phenyl-2-((pyridin-3-yl)formamido)propanoic acidYield 96%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 3-phenyl-2-[(pyridine-3-carbonyl)-amino]-propionic acid methylester (1.2 g, 4.2 mmol) in methanol (10 mL), THF (30 mL) was added LiOH (0.885 g, 21.1 mmol) dissolved in water (10 mL). The mixture was allowed to stir at room temperature (25° C.) over a period of 2 hrs. THF was evaporated from reaction mixture, acidified with 1.5N HCl then extracted with ethylacetate (200 mL) and concentrated to obtain product as yellow color solid (1.0 g, 96%).

Workup

  1. customTHF was evaporated from reaction mixture
  2. extractionthen extracted with ethylacetate (200 mL)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-9c9af8d1d3c4426e9590a4e408e73ce5
Source dataset
uspto-grants-2014_09
Patent number
US08846721B2

Reaction notes

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