Water → HCID 18670149, compound
Reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[C:4]1[CH2:8][NH:9][C:10](=[O:12])[CH3:11].[CH3:13][Si:14]([CH3:21])([CH3:20])[CH2:15][CH2:16][O:17][CH2:18]Cl.O>CN(C)C=O.C(OCC)(=O)C>[CH3:13][Si:14]([CH3:21])([CH3:20])[CH2:15][CH2:16][O:17][CH2:18][N:3]1[CH:7]=[CH:6][N:5]=[C:4]1[CH2:8][NH:9][C:10](=[O:12])[CH3:11]Participants
Procedure
Under ice-cooling, 0.08 g of sodium hydride (60% oily) was added to a solution of 0.31 g of N-(imidazol-2-ylmethyl)acetamide in N,N-dimethylformamide (10 ml). After stirring for 15 minutes, a solution of 0.35 ml of 2-(trimethylsilyl)ethoxymethyl chloride in N,N-dimethylformamide (1 ml) was dropped thereinto and the resulting mixture was stirred at room temperature for additional 16 hours. Then the reaction mixture was distributed into water and ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate. After concentrating under reduced pressure, the residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol) to thereby give 0.16 g of the title compound as a colorless oily substance.
Workup
- temperatureUnder ice-cooling
- stirringthe resulting mixture was stirred at room temperature for additional 16 hours
- washThe organic layer was washed with water
- dry with materialdried over anhydrous magnesium sulfate
- concentrationAfter concentrating under reduced pressure
- customthe residue was purified by silica gel column chromatography (eluted with dichloromethane/methanol)
Sources & evidence
- ORD record
- ord-c14974c2712e4042a06800136c02682d
- Source dataset
- uspto-grants-2003_02
- Patent number
- US06518423B1
Reaction notes
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