Hydrochloric Acid → 2-(4-Methoxy-3-((4-(trifluoromethyl)benzamido)methyl)benzyl)butanoic acid

HRID 1816563Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]([CH2:7][CH:8]([CH2:14][CH3:15])[C:9]([O:11]CC)=[O:10])=[CH:5][C:4]=1[CH2:18][NH:19][C:20](=[O:31])[C:21]1[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=1.[OH-].[Na+].Cl>C(O)C>[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]([CH2:7][CH:8]([CH2:14][CH3:15])[C:9]([OH:11])=[O:10])=[CH:5][C:4]=1[CH2:18][NH:19][C:20](=[O:31])[C:21]1[CH:22]=[CH:23][C:24]([C:27]([F:28])([F:29])[F:30])=[CH:25][CH:26]=1

Participants

Conditions

Temperature: 70 °C

Procedure

0.59 g of ethyl 2-[4-methoxy-3-({[4-(trifluoromethyl)benzoyl]amino}methyl)benzyl]butanoate was dissolved in 5 ml ethanol, and 2 ml of 1 N sodium hydroxide was added, and the mixture was stirred at 70° C. for 4 hours. The reaction mixture was ice-cooled and neutralized with 1N hydrochloric acid, followed by extracting with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and the solvent was evaporated, to give 0.50 g of 2-[4-methoxy-3-({[4-(trifluoromethyl)benzoyl]amino}methyl]benzyl]butanoic acid.

Workup

temperaturecooled
extractionby extracting with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over anhydrous sodium sulfate
customthe solvent was evaporated

Sources & evidence

ORD record: ord-edf0654001e140f082ce7a32e36e49cd
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06884821B1

Reaction notes

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