Sodium Chloride → (S)-4-BENZYL-3-(3-PHENYLPROPANOYL)OXAZOLIDIN-2-ONE

HRID 1768853Notes

Reaction equation

HRID 1768853 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.[C:19]1([CH2:25][CH2:26][C:27](Cl)=[O:28])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[Cl-].[Na+]>CCCCCC.O1CCCC1>[CH2:6]([C@H:13]1[CH2:17][O:16][C:15](=[O:18])[N:14]1[C:27](=[O:28])[CH2:26][CH2:25][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 64801Benzenepropanoyl chlorideHCID 736225(S)-4-Benzyl-2-oxazolidinoneHCID 178418339Butyllithium

Product 1

HCID 10957844(S)-4-BENZYL-3-(3-PHENYLPROPANOYL)OXAZOLIDIN-2-ONEYield 78%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

48.1 ml (77 mmole) of butyllithium (as a 1.6M solution in hexane) were added dropwise, at -78° C. and under an atmosphere of nitrogen, to a solution of 12.41 g (70 mmole) of (4S)-(-)-4-benzyl-2-oxazolidinone in 200 ml of anhydrous tetrahydrofuran, and the mixture was stirred for 30 minutes. At the end of this time, a solution of 13.0 g (77 mmole) of 3-phenylpropionyl chloride in 100 ml of anhydrous tetrahydrofuran was slowly added dropwise to the mixture, and the mixture was stirred for 1 hour. The mixture was then mixed with a saturated aqueous solution of sodium chloride and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated by distillation under reduced-pressure. The residue was purified by column chromatography through silica gel (using a 1:4 by volume mixture of ethyl acetate and hexane as the eluent) to afford 16.8 g (yield 78%) of the title compound as white crystals, melting at 92°-95° C.

Workup

  1. stirringthe mixture was stirred for 1 hour
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated by distillation under reduced-pressure
  5. customThe residue was purified by column chromatography through silica gel (
  6. additionby volume mixture of ethyl acetate and hexane as the eluent)

Sources & evidence

ORD record
ord-5e640267111c40d3bca8f84f36359bb9
Source dataset
uspto-grants-1995_01
Patent number
US05378689

Reaction notes

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