Water → HCID 178450421, compound
Reaction equation
[NH2:1][CH:2]([CH2:6][O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[C:3]([NH2:5])=[O:4].[S:12](Cl)(Cl)=O.O>ClCCl.C(N(CC)CC)C>[C:8]([O:7][CH2:6][C:2]1[C:3]([OH:4])=[N:5][S:12][N:1]=1)([CH3:11])([CH3:10])[CH3:9]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -78 °C
Procedure
After dissolving 8.17 g of 2-amino-3-(tert-butoxy)propionamide in 150 ml of dichloromethane, 16.37 ml of triethylamine was added and the solution was cooled to −78° C., and then 4.10 ml of thionyl chloride was added dropwise while stirring at below −50° C. After stirring for 30 minutes, the temperature was raised to room temperature and stirring was continued overnight. Water was added to the reaction solution, and extraction was performed with dichloromethane. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered with silica gel. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (solvent: n-hexane/ethyl acetate) to obtain the title compound (1.98 g, 21% yield).
Workup
- additionwas added
- stirringAfter stirring for 30 minutes
- temperaturethe temperature was raised to room temperature
- stirringstirring
- washThe organic layer was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered with silica gel
- distillationThe solvent was distilled off under reduced pressure
- customthe residue was purified by silica gel column chromatography (solvent: n-hexane/ethyl acetate)
Sources & evidence
- ORD record
- ord-e239c92e238e49d39b27cd4e8a8585ea
- Source dataset
- uspto-grants-2007_09
- Patent number
- US07265108B2
Reaction notes
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