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

HRID 2176877Notes

Reaction equation

HRID 2176877 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-a3eb33d9c3a042f39a815193bf05bf59
Source dataset
uspto-grants-2015_06
Patent number
US09067888B2

Reaction notes

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