2-Ethylbutyryl chloride → (+)-2-ethyl-N-{4-[2-(2-methyl-5-oxo-4-phenyl-4-propyl-4,5-dihydro-imidazol-1-yl)-acetyl]-phenyl}-butyramide
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:26])[CH2:9][N:10]2[C:14](=[O:15])[C:13]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)([CH2:16][CH2:17][CH3:18])[N:12]=[C:11]2[CH3:25])=[CH:4][CH:3]=1.[CH2:27]([CH:29]([CH2:33][CH3:34])[C:30](Cl)=[O:31])[CH3:28]>>[CH2:27]([CH:29]([CH2:33][CH3:34])[C:30]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:26])[CH2:9][N:10]2[C:14](=[O:15])[C:13]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)([CH2:16][CH2:17][CH3:18])[N:12]=[C:11]2[CH3:25])=[CH:6][CH:7]=1)=[O:31])[CH3:28]Participants
3
Procedure
Synthesis in analogy to Example 8 starting from enantiomerically pure 3-[2-(4-amino-phenyl)-2-oxo-ethyl]-2-methyl-5-phenyl-5-propyl-3,5-dihydro-imidazol-4-one and 2-ethyl-butyryl chloride to yield (−)-2-ethyl-N-{4-[2-(2-methyl-5-oxo-4-phenyl-4-propyl-4,5-dihydro-imidazol-1-yl)-acetyl]-phenyl}-butyramide. LC/MS at 254 nm; [M+H] 448; Rt=3.313 min; optical rotation=−8.2°, c=1.0 in methanol.
Sources & evidence
- ORD record
- ord-73e705a14d8b49b2b908e85617452a5e
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07786155B2
Reaction notes
Loading…