Hydrochloric Acid → 2-(4-Methoxy-3-((4-(trifluoromethyl)benzamido)methyl)benzyl)butanoic acid
Reaction equation
[CH2:1]([CH:3]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([CH2:18][NH:19][C:20](=[O:31])[C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=2)[CH:11]=1)[C:4]([O:6]CC)=[O:5])[CH3:2].CO.[OH-].[Na+].Cl>O>[CH2:1]([CH:3]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([CH2:18][NH:19][C:20](=[O:31])[C:21]2[CH:22]=[CH:23][C:24]([C:27]([F:29])([F:28])[F:30])=[CH:25][CH:26]=2)[CH:11]=1)[C:4]([OH:6])=[O:5])[CH3:2]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
A mixture of ethyl 2-ethyl-3-[3-[4-(trifluoromethyl)benzoylaminomethyl]-4-methoxyphenyl]propanoate (240 mg, 0.549 mmol), methanol (6 mL) and 2.5 mol/L aqueous solution of sodium hydroxide (2 mL) was stirred for 4 hours under heating at 50° C. After cooling, water (20 mL) was added and the mixture was made acidic with 1 mol/L hydrochloric acid, which was then extracted with ethyl acetate. The organic later was washed with water and brine, dried over anhydrous sodium sulfate, and then concentrated to afford 222 mg (99%) of the title compound as colorless crystals. Further, these were recrystallized from diethyl ether-n-hexane, thus affording 161 mg (72%) of purified title compound as colorless needles.
Workup
- temperatureAfter cooling
- extractionwas then extracted with ethyl acetate
- washThe organic later was washed with water and brine
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-8b3b781c090443d4b29c4da573960419
- Source dataset
- uspto-grants-2006_05
- Patent number
- US07049342B2
Reaction notes
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