Vinyl Acetate → HCID 59157701, compound
Reaction equation
C([O:4][CH:5]=[CH2:6])(=O)C.[NH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15].ON1[C:24]2C=CC=C[C:23]=2N=N1.CCN=C=NCCCN(C)C>O.C(Cl)(Cl)Cl>[C:14]([O:13][C:12](=[O:18])[NH:11][CH2:10][CH2:9][CH2:8][NH:7][C:5](=[O:6])[CH2:4][CH:23]=[CH2:24])([CH3:15])([CH3:17])[CH3:16]Participants
Procedure
To a chloroform solution (58 mL) of vinyl acetate (500 mg, 5.81 mmol) were added tert-butyl N-(3-aminopropyl)carbamate (2.02 g, 11.6 mmol), 1-hydroxybenzotriazole (0.86 g, 6.39 mmol) and WSC (1.56 g, 8.13 mmol), and the mixture was stirred overnight at room temperature. To the reaction solution was added water and the resulting mixture was extracted with chloroform. The organic layer was washed with a saturated aqueous solution of ammonium chloride and brine, and dried with anhydrous magnesium sulfate. The drying agent was filtered off, and the solvent was evaporated under reduced pressure. Thus obtained residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:1, ethyl acetate) to obtain the title compound (1.32 g, 94%) as a colorless powder.
Workup
- extractionthe resulting mixture was extracted with chloroform
- washThe organic layer was washed with a saturated aqueous solution of ammonium chloride and brine
- dry with materialdried with anhydrous magnesium sulfate
- filtrationThe drying agent was filtered off
- customthe solvent was evaporated under reduced pressure
- customThus obtained residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:1, ethyl acetate)
Sources & evidence
- ORD record
- ord-e947e1d3d2a34733b556ba039184110a
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07973012B2
Reaction notes
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