Ethyl bromoacetate → Ethyl[(55)-3-(2,4-dimethoxybenzyl)-2-oxo-5-(propan-2-yl)imidazolidin-1-yl]acetate
Reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:6]=1[CH2:7][N:8]1[CH2:12][C@H:11]([CH:13]([CH3:15])[CH3:14])[NH:10][C:9]1=[O:16].Br[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26]>CN(C=O)C>[CH2:28]([O:27][C:25](=[O:26])[CH2:24][N:10]1[C@@H:11]([CH:13]([CH3:15])[CH3:14])[CH2:12][N:8]([CH2:7][C:6]2[CH:17]=[CH:18][C:19]([O:21][CH3:22])=[CH:20][C:5]=2[O:4][CH3:3])[C:9]1=[O:16])[CH3:29]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Sodium hydride (60%, 380 mg) was added to a solution of (4S)-1-(2,4-dimethoxybenzyl)-4-(propan-2-yl)imidazolidin-2-one (2.4 g) in DMF (35 mL), and the mixture was stirred for 20 min. Ethyl bromoacetate (1.14 mL) was added thereto, and the mixture was stirred at 90° C. for 1 hr. Additional ethyl bromoacetate (1.14 g) and sodium hydride (60%, 380 mg) were added thereto, and the resulting mixture was further stirred at 90° C. for 1 hr. After the solvent was distilled off under reduced pressure, the residue was purified by column chromatography (silica gel cartridge, hexane/ethyl acetate) to afford ethyl[(55)-3-(2,4-dimethoxybenzyl)-2-oxo-5-(propan-2-yl)imidazolidin-1-yl]acetate (1.5 g).
Workup
- stirringthe mixture was stirred at 90° C. for 1 hr
- stirringthe resulting mixture was further stirred at 90° C. for 1 hr
- distillationAfter the solvent was distilled off under reduced pressure
- customthe residue was purified by column chromatography (silica gel cartridge, hexane/ethyl acetate)
Sources & evidence
- ORD record
- ord-5888cc7f2a17463d9bf7d9e15924fcec
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08796272B2
Reaction notes
Loading…