Ethyl Acetate → HCID 178453494, compound
Reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([CH2:17][O:18][Si](C(C)(C)C)(C)C)[CH2:13][CH2:12]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>O1CCCC1>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C@H:11]1[CH2:12][CH2:13][C@H:14]([CH2:17][OH:18])[CH2:15][CH2:16]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
In 10 ml of dry tetrahydrofuran was dissolved 1.05 g of N-t-butoxycarbonyl-2-(trans-4-t-butyldimethylsilyloxymethylcyclohexyl)ethylamine, and 8.48 ml of tetrabutylammonium fluoride (1.0M tetrahydrofuran solution) were added dropwise thereto with stirring under ice-cooling, and the resulting mixture was stirred at room temperature overnight. To the reaction mixture were added 150 ml of ethyl acetate, and the mixture was washed with an aqueous sodium bicarbonate solution and an aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography employing cyclohexane-ethyl acetate (2:1) as an eluting solvent to obtain 471 mg of the desired compound as a colorless crystalline solid.
Workup
- additionwere added dropwise
- temperaturecooling
- stirringthe resulting mixture was stirred at room temperature overnight
- washthe mixture was washed with an aqueous sodium bicarbonate solution
- dry with materialan aqueous sodium chloride solution and dried over anhydrous magnesium sulfate
- distillationthe solvent was distilled off under reduced pressure
- customThe residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-109b032540c746b998594cd4cc4ff359
- Source dataset
- uspto-grants-1998_12
- Patent number
- US05843973
Reaction notes
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