Triethylamine → Ethyl 2-isopropoxy-3-[4-methoxy-3-(4-trifluoromethylphenylacetylamino)phenyl]propanoate
Reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:10][CH:11]([O:17][CH:18]([CH3:20])[CH3:19])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[F:21][C:22]([F:34])([F:33])[C:23]1[CH:28]=[CH:27][C:26]([CH2:29][C:30](O)=[O:31])=[CH:25][CH:24]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.C(N(CC)CC)C>O1CCCC1.O>[CH:18]([O:17][CH:11]([CH2:10][C:4]1[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([NH:1][C:30](=[O:31])[CH2:29][C:26]2[CH:25]=[CH:24][C:23]([C:22]([F:33])([F:21])[F:34])=[CH:28][CH:27]=2)[CH:3]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13])([CH3:19])[CH3:20]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
0.3 g of ethyl 3-(3-amino-4-methoxyphenyl)-2-isopropoxypropanoate and 0.218 g of (α,α,α-trifluoro-p-tolyl)acetic acid were dissolved in 7 ml tetrahydrofuran, and 0.22 g of carbonyldiimidazole and 0.23 ml triethylamine were added thereto, and the mixture was stirred at 50° C. for 2 hours. The reaction mixture was ice-cooled, and water was added followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and the solvent was evaporated. The residue was subjected to silica gel column chromatography, and from fractions eluted with hexane-ethyl acetate (6:1), 0.34 g of ethyl 2-isopropoxy-3-[4-methoxy-3-(4-trifluoromethylphenylacetylamino)phenyl]propanoate was obtained.
Workup
- temperaturecooled
- extractionfollowed by extraction with ethyl acetate
- washThe organic layer was washed with brine
- dry with materialdried over anhydrous magnesium sulfate
- customthe solvent was evaporated
- washfrom fractions eluted with hexane-ethyl acetate (6:1)
Sources & evidence
- ORD record
- ord-cd9261a483e94742b7b1dbf57b5613be
- Source dataset
- uspto-grants-2005_04
- Patent number
- US06884821B1
Reaction notes
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