Bromoacetonitrile → (S)-3-(4-bromo-2-methoxy-phenyl)-4-((S)-4-isopropyl-2-oxo-oxazolidin-3-yl)-4-oxo-butyronitrile
Reaction equation
[CH:1]([N-:4]C(C)C)(C)[CH3:2].[Li+].[Br:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17]([N:19]2[C@@H:23]([CH:24]([CH3:26])[CH3:25])[CH2:22][O:21][C:20]2=[O:27])=[O:18])=[C:12]([O:28][CH3:29])[CH:11]=1.BrCC#N.[NH4+].[Cl-]>C1COCC1>[Br:9][C:10]1[CH:15]=[CH:14][C:13]([C@@H:16]([C:17]([N:19]2[C@@H:23]([CH:24]([CH3:26])[CH3:25])[CH2:22][O:21][C:20]2=[O:27])=[O:18])[CH2:2][C:1]#[N:4])=[C:12]([O:28][CH3:29])[CH:11]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Lithium diisopropylamide (2.0 M in heptane/THF/ethylbenzene, 1.58 mL, 3.16 mmol) was added to a solution of (S)-3-[2-(4-bromo-2-methoxy-phenyl)-acetyl]-4-isopropyl-oxazolidin-2-one (1.126 g, 3.16 mmol) in THF (11 mL) under argon atmosphere at −78° C. The mixture was stirred for 15 minutes and bromoacetonitrile (0.23 mL, 3.32 mmol) was added at −78° C. The mixture was stirred for 3 hours at 0° C., and then a saturated solution of NH4Cl was added. The mixture was extracted with EtOAc, and the combined organic extracts were washed with brine, dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified via flash chromatography (hexane/EtOAc, 85/15) to give 755 mg (60% yield) of (S)-3-(4-bromo-2-methoxy-phenyl)-4-((S)-4-isopropyl-2-oxo-oxazolidin-3-yl)-4-oxo-butyronitrile as a white solid.
Workup
- stirringThe mixture was stirred for 3 hours at 0° C.
- extractionThe mixture was extracted with EtOAc
- washthe combined organic extracts were washed with brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- customevaporated under reduced pressure
- customThe residue was purified via flash chromatography (hexane/EtOAc, 85/15)
Sources & evidence
- ORD record
- ord-f802fb5a807045999ad86eadd2621f34
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07776910B2
Reaction notes
Loading…