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

HRID 82478Notes

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

Participants

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

extractionextracted with ethylacetate (100 mL)
dry with materialdried over sodium sulphate
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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