Phthalimide potassium salt → HCID 59296009, compound
Reaction equation
[N+](C1C=C(S(O[CH2:14][C@:15]2([CH3:18])[CH2:17][O:16]2)(=O)=O)C=CC=1)([O-])=O.[C:19]1(=[O:29])[NH:23][C:22](=[O:24])[C:21]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:20]12.[K]>CN(C)C=O>[CH3:14][C@@:15]1([CH2:18][N:23]2[C:19](=[O:29])[C:20]3[C:21](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:22]2=[O:24])[CH2:17][O:16]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a solution of (2S)-(2-methyloxiran-2-yl)methyl 3-nitrobenzenesulphonate (1.913 g, 7 mmoles) in dry dimethylformamide (15 ml), was added potassium phthalimide (1.304 g, 7 mmoles). The mixture was stirred at 50° C. for 5 h and then cooled to room temperature. The resulting mixture was partitioned between ethyl acetate and water. The aqueous phase was washed with ethyl acetate (2×100 ml) and the combined organic extracts were washed with water (3×100 ml), saturated brine solution, dried over sodium sulfate and concentrated in vacuo to leave a crude orange wax. Purification by chromatography (silica, 20% ethyl acetate in iso-hexane) afforded the subtitle compound as a white solid (0.864 g).
Workup
- temperaturecooled to room temperature
- customThe resulting mixture was partitioned between ethyl acetate and water
- washThe aqueous phase was washed with ethyl acetate (2×100 ml)
- washthe combined organic extracts were washed with water (3×100 ml), saturated brine solution
- dry with materialdried over sodium sulfate
- concentrationconcentrated in vacuo
- customto leave a crude orange wax
- customPurification by chromatography (silica, 20% ethyl acetate in iso-hexane)
Sources & evidence
- ORD record
- ord-cc2564ca990f441dbce15b99d8ded137
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07709500B2
Reaction notes
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