Isobutyl 3,4-epoxybutyrate → 2-Methylpropyl 3-carbamoylmethyl-Beta-hydroxy2-(1-methylethyl)-4-oxo-1-imidazolidinebutanoate
Reaction equation
[CH3:1][CH:2]([CH:4]1[NH:8][CH2:7][C:6](=[O:9])[N:5]1[CH2:10][C:11]([NH2:13])=[O:12])[CH3:3].[O:14]1[CH2:24][CH:15]1[CH2:16][C:17]([O:19][CH2:20][CH:21]([CH3:23])[CH3:22])=[O:18]>C(O)CCCC>[C:11]([CH2:10][N:5]1[C:6](=[O:9])[CH2:7][N:8]([CH2:24][CH:15]([OH:14])[CH2:16][C:17]([O:19][CH2:20][CH:21]([CH3:23])[CH3:22])=[O:18])[CH:4]1[CH:2]([CH3:1])[CH3:3])(=[O:12])[NH2:13]Participants
Procedure
A solution of 1.2 g (6.4 mmol) of 2-(1-methylethyl)-5-oxo-1-imidazolidineacetamide and 2 g of 2-methylpropyl 3,4-epoxybutanoate in 40 ml of anhydrous pentanol was stirred at 80° C. for 48 hours. The solvent was evaporated under reduced pressure. The residue was dissolved in 15 ml of 15% HCl, washed with 2×25 ml dichloromethane, basified with sodium carbonate with sodium carbonate and extracted with 3×35 ml dichloromethane. The organic layer was dried and evaporated to afford 1.08 g of the title compound as a colorless oil (mixture of two diastereoisomers, Rf 0.27 and 0.32 respectively (dichloromethane/methanol 9:1; silica gel plates). Mass spectrum (E.I., 70 eV, 1.5 mA), m/z=300 (M+ --C3H7). IR spectrum (neat): 3400, 3200, 1730 and 1690 cm-1.
Workup
- customThe solvent was evaporated under reduced pressure
- dissolutionThe residue was dissolved in 15 ml of 15% HCl
- washwashed with 2×25 ml dichloromethane
- extractionextracted with 3×35 ml dichloromethane
- customThe organic layer was dried
- customevaporated
Sources & evidence
- ORD record
- ord-11cbbbc40d1747bba0b09aaaa4118340
- Source dataset
- uspto-grants-1989_09
- Patent number
- US04868313
Reaction notes
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