Hydrochloric Acid → 5-Chloro-2-{[4-({[3-(furan-3-yl)phenyl]carbonyl}amino)butanoyl]amino}benzoic acid

HRID 1626723Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:12][C:13](=[O:31])[CH2:14][CH2:15][CH2:16][NH:17][C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]3[CH:30]=[CH:29][O:28][CH:27]=3)[CH:21]=2)=[O:19])=[C:6]([CH:11]=1)[C:7]([O:9]C)=[O:8].[OH-].[Na+].Cl>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:12][C:13](=[O:31])[CH2:14][CH2:15][CH2:16][NH:17][C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]3[CH:30]=[CH:29][O:28][CH:27]=3)[CH:21]=2)=[O:19])=[C:6]([CH:11]=1)[C:7]([OH:9])=[O:8]

Participants

Conditions

Temperature: 50 °C

Procedure

1.22 g (2.8 mmol) of methyl 5-chloro-2-{[4-({[3-(furan-3-yl)phenyl]carbonyl}amino)butanoyl]amino}benzoate was dissolved in 12 mL of tetrahydrofuran (THF). 1N aqueous sodium hydroxide was added at room temperature, and the mixture was stirred at 50° C. for 1.5 hours. After cooling the mixture, 1N hydrochloric acid was added to acidify the reaction mixture, and the solvent was distilled off under reduced pressure. Thereafter, water was added to the residue. Solids were collected by filtration, followed by washing with water, thereby giving 1.07 g of the target 5-chloro-2-{[4-({[3-(furan-3-yl)phenyl]carbonyl}amino)butanoyl]amino}benzoic acid (yield: 91%).

Workup

additionwas added
distillationthe solvent was distilled off under reduced pressure
additionThereafter, water was added to the residue
filtrationSolids were collected by filtration
washby washing with water

Sources & evidence

ORD record: ord-17f566008a55428286c5533bc88cc2d5
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785473B2

Reaction notes

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