Acetone → HCID 58765446, compound
Reaction equation
N1C2[C:4](=[CH:5][CH:6]=CC=2)[CH2:3][C@H:2]1[C:10](O)=O.[CH3:13]C(C)=O.[C:17](=[O:20])([O-])[O-:18].[K+].[K+].CI.[CH3:25][N:26]([CH3:29])[CH:27]=O>>[CH3:13][O:18][C:17]([C@@H:27]1[CH2:6][C:5]2[C:25](=[CH:10][CH:2]=[CH:3][CH:4]=2)[N:26]1[CH3:29])=[O:20]Participants
Procedure
(S)-(−)-indoline-2-carboxylic acid (2.0 g) was dissolved to a mixture of acetone (20 ml) and N,N-dimethylformamide (20 ml), and potassium carbonate (6.78 g) and methyliodide (3.05 ml) were added at room temperature. The reactive mixture was stirred at room temperature over night, and then filtered. The filtrate was concentrated by vacuum concentration and the obtained residue was diluted with ethyl acetate. The solution is poured into water and the water layer has been extracted by ethyl acetate. The organic layer was sequentially washed with water and saturated brine, and then dried by anhydrous sodium sulfate. The residue by removal of the solvent was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to give a title compound (1.7 g) having the following physical properties.
Workup
- additionwere added at room temperature
- filtrationfiltered
- concentrationThe filtrate was concentrated by vacuum concentration
- additionthe obtained residue was diluted with ethyl acetate
- additionThe solution is poured into water
- extractionthe water layer has been extracted by ethyl acetate
- washThe organic layer was sequentially washed with water and saturated brine
- dry with materialdried by anhydrous sodium sulfate
- customThe residue by removal of the solvent
- customwas purified by silica gel column chromatography (hexane:ethyl acetate=4:1)
Sources & evidence
- ORD record
- ord-e2ac7cc6e6124b9295bdf5724e3fd106
- Source dataset
- uspto-grants-2006_12
- Patent number
- US07153852B2
Reaction notes
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