3-(2-chloro-phenoxy)-4-((S)-3-methoxy-1-methoxycarbonyl-propylamino)-but-2-enoic acid ethyl ester → (S)-2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methoxy-butyric acid methyl ester
Reaction equation
C([O:3][C:4](=O)[CH:5]=[C:6]([O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[Cl:25])[CH2:7][NH:8][C@H:9]([C:14]([O:16][CH3:17])=[O:15])[CH2:10][CH2:11][O:12][CH3:13])C>C(#N)C>[CH3:17][O:16][C:14](=[O:15])[C@@H:9]([N:8]1[CH2:7][C:6]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:25])=[CH:5][C:4]1=[O:3])[CH2:10][CH2:11][O:12][CH3:13]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 150 °C
Procedure
A solution of 3-(2-chloro-phenoxy)-4-((S)-3-methoxy-1-methoxycarbonyl-propylamino)-but-2-enoic acid ethyl ester (112 mg, 0.29 mmol) in acetonitrile (2 mL) was placed in a sealed microwave reaction tube and heated in a microwave reactor at 130° C. for 2 h, 150° C. for 2 h, and 160° C. for 3 h. The mixture was then concentrated in vacuo and purified by AnaLogix IntelliFlash flash chromatography (8 g column, 20% ethyl acetate/hexanes to 70% ethyl acetate/hexanes) which afforded (S)-2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methoxy-butyric acid methyl ester (71 mg, 39% over two steps) as a clear colorless oil.
Workup
- concentrationThe mixture was then concentrated in vacuo
- custompurified by AnaLogix IntelliFlash flash chromatography (8 g column, 20% ethyl acetate/hexanes to 70% ethyl acetate/hexanes) which
Sources & evidence
- ORD record
- ord-18fcb1831fb340a492c3b4815df17a09
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07741327B2
Reaction notes
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