Methyl iodide → (S)-3-((R)-2-(4-methoxyphenyl)propanoyl)-4-benzyloxazolidin-2-one
Reaction equation
[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:24])[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:25]([N-]C(C)C)(C)C.[Li+].IC>C1COCC1>[CH3:23][O:22][C:19]1[CH:18]=[CH:17][C:16]([C@@H:15]([CH3:25])[C:14]([N:9]2[C@@H:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:12][O:11][C:10]2=[O:13])=[O:24])=[CH:21][CH:20]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -20 °C
Procedure
A solution of (S)-4-benzyl-3-(2-(4-methoxyphenyl)acetyl)oxazolidin-2-one (1.00 g, 3.07 mmol) in dry THF (10 ml) was added to lithium diisopropyl amide (400 mg, 3.69 mmol, 0.1 M) at −78° C. The reaction mixture was stirred for 2 h. Iodomethane (2.00 g, 14.1 mmol) was added to the reaction mixture and warmed to −20° C. and stirred for another 2 h. The reaction mixture was quenched with saturated ammonium chloride solution (20 ml) and extracted with ethyl acetate (3×25 ml). The combined organic layers was dried over anhydrous sodium sulfate, filtered and concentrated. The crude compound was purified by column chromatography over silica gel (60-120 mesh) using ethyl acetate (10%) in petroleum ether as eluent to afford 350 mg (33.8%) of (S)-3-((R)-2-(4-methoxyphenyl)propanoyl)-4-benzyloxazolidin-2-one as light yellow solid.
Workup
- stirringstirred for another 2 h
- customThe reaction mixture was quenched with saturated ammonium chloride solution (20 ml)
- extractionextracted with ethyl acetate (3×25 ml)
- dry with materialThe combined organic layers was dried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe crude compound was purified by column chromatography over silica gel (60-120 mesh)
Sources & evidence
- ORD record
- ord-237201cdb0664dc8b47b895502056f45
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09067888B2
Reaction notes
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