HCID 67504052, compound → 2-[4-(2-Chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4,4,4-trifluoro-butyric acid methyl ester
Reaction equation
C([O:3][C:4](=O)[CH:5]=[C:6]([O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[Cl:26])[CH2:7][NH:8][CH:9]([C:15]([O:17][CH3:18])=[O:16])[CH2:10][C:11]([F:14])([F:13])[F:12])C>C(#N)C>[CH3:18][O:17][C:15](=[O:16])[CH:9]([N:8]1[CH2:7][C:6]([O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:26])=[CH:5][C:4]1=[O:3])[CH2:10][C:11]([F:14])([F:13])[F:12]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 150 °C
Procedure
A solution of 3-(2-chloro-phenoxy)-4-(3,3,3-trifluoro-1-methoxycarbonyl-propylamino)-but-2-enoic acid ethyl ester (410 mg, 1.00 mmol) in acetonitrile (4 mL) was placed in a sealed microwave reaction tube and heated in a microwave reactor at 150° C. for 3 h. The mixture was then cooled to room temperature and concentrated in vacuo with silica gel (2 g). Purification by Biotage flash chromatography (Aspire 40 g column, 16% ethyl acetate/hexanes to 33% ethyl acetate/hexanes) afforded 2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4,4,4-trifluoro-butyric acid methyl ester (153 mg, 17% over two steps) as a yellow oil.
Workup
- temperatureThe mixture was then cooled to room temperature
- concentrationconcentrated in vacuo with silica gel (2 g)
- customPurification by Biotage flash chromatography (Aspire 40 g column, 16% ethyl acetate/hexanes to 33% ethyl acetate/hexanes)
Sources & evidence
- ORD record
- ord-70c1e034417b4b299959fb6ec94bd07f
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07741327B2
Reaction notes
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