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Hydrochloric Acid → 3(1H-indol-3-yl)-2-[pyridine-3-carbonyl]-amino-propionic acid

HRID 82478
Notes
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Reaction equation

HRID 82478 reaction equation
C[O:2][C:3](=[O:24])[C:4]([NH2:23])([C:15]([C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)=[O:16])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][CH:7]=1.C1COCC1.[Li+].[OH-].Cl>CO.O>[NH:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]([CH2:5][C:4]([NH2:23])([C:15]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)=[O:16])[C:3]([OH:24])=[O:2])=[CH:7]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 866749223(1H-indol-3-yl)-2-[pyridine-3-carbonyl]-amino-propionic acid methylester

Product 1

HCID 673452343(1H-indol-3-yl)-2-[pyridine-3-carbonyl]-amino-propionic acidYield 99%

Reagents, catalysts & solvents 2

HCID 887
Methanol
Solvent
HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 3(1H-indol-3-yl)-2-[pyridine-3-carbonyl]-amino-propionic acid methylester (0.5 g, 1.6 mmol), in methanol (5 mL), THF (9 mL) was added LiOH (0.39 g, 7.70 mmol), dissolved in water (3 mL), The mixture was allowed to stir at room temperature (25° C.) over 2 h. Stripped off solvent, acidified reaction mass with 1.5N HCl, extracted with ethylacetate (100 mL) dried over sodium sulphate and concentrated to obtain product as colorless solid (0.48 g, 99%).

Workup

  1. extractionextracted with ethylacetate (100 mL)
  2. dry with materialdried over sodium sulphate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-8452d0274a8146efaf00e68d3255a582
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08846721B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes