(S)-4-Benzyl-2-oxazolidinone → (S)-4-Benzyl-3-[2-(4-methoxyphenyl)acetyl]-2-oxazolidinone

HRID 1896241Notes

Reaction equation

HRID 1896241 reaction equation
C([Li])CCC.[CH2:6]([C@H:13]1[CH2:17][O:16][C:15](=[O:18])[NH:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][C:28](Cl)=[O:29])=[CH:23][CH:22]=1>C1COCC1>[CH2:6]([C@H:13]1[CH2:17][O:16][C:15](=[O:18])[N:14]1[C:28](=[O:29])[CH2:27][C:24]1[CH:25]=[CH:26][C:21]([O:20][CH3:19])=[CH:22][CH:23]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 736225(S)-4-Benzyl-2-oxazolidinoneHCID 27346884-Methoxyphenylacetyl chlorideHCID 178418339Butyllithium

Product 1

HCID 10758405(S)-4-Benzyl-3-[2-(4-methoxyphenyl)acetyl]-2-oxazolidinoneYield 82.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

n-Butyllithium (15.4 ml, 24.7 mmol, 1.6 M) was added to a solution of (S)-4-benzyl oxazolidinone (4.00 g, 22.5 mmol) in dry THF (100 ml) at −78° C. and stirred for 30 min. Then p-methoxyphenyl acetyl chloride (6.50 ml, 29.3 mmol) in THF (50 ml) was added to the reaction mixture at −78° C. The reaction mixture was allowed to warm up to room temperature and stirred overnight. It was then quenched with saturated ammonium chloride solution (50 ml) and extracted with ethyl acetate (3×50 ml). The crude compound was purified by column chromatography over silica gel (60-120 mesh) using ethyl acetate (7%) in petroleum ether as eluent to afford 6.0 g (82.5%) of (S)-4-benzyl-3-(2-(4-methoxyphenyl)acetyl)oxazolidin-2-one as an off-white color solid.

Workup

  1. stirringstirred overnight
  2. customIt was then quenched with saturated ammonium chloride solution (50 ml)
  3. extractionextracted with ethyl acetate (3×50 ml)
  4. customThe crude compound was purified by column chromatography over silica gel (60-120 mesh)

Sources & evidence

ORD record
ord-020e254719614b8db1c21a0eea1d24d1
Source dataset
uspto-grants-2013_08
Patent number
US08518948B2

Reaction notes

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