Phenylacetyl chloride → (4S)-3-(2-Phenylacetyl)-4-(phenylmethyl)-2-oxazolidinone

HRID 1584491Notes

Reaction equation

HRID 1584491 reaction equation
[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[C:19]1([CH2:25][C:26](Cl)=[O:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(OCC)(=O)C.CCCCCC>O1CCCC1>[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:26](=[O:27])[CH2:25][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 7679Phenylacetyl chlorideHCID 736225(S)-4-Benzyl-2-oxazolidinoneHCID 21226206Ethyl acetate hexaneHCID 178418339Butyllithium

Product 1

HCID 11130206(4S)-3-(2-Phenylacetyl)-4-(phenylmethyl)-2-oxazolidinone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Combine (S)-4-benzyl-2-oxazolidinone (22.9 g, 129 mmol) and tetrahydrofuran (120 mL). Cool in a dry-ice acetone bath. Add dropwise a solution of n-butyl lithium (52 mL, 2.5 M, 130 mmol). After 15 minutes, slowly add a solution of phenylacetyl chloride (20 g, 129.4 mmol) in tetrahydrofuran (50 mL). After 20 minutes, warm to ambient temperature. After 2 hours, quench the reaction mixture by the addition of a saturated aqueous sodium bicarbonate solution. Separate the layers and extract the aqueous layer with diethyl ether. Combine the organic layers, dry over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 15% ethyl acetate/hexane. Combine the product containing fractions, evaporate, and recrytallize from diethyl ether/hexane to give (S)-4-benzyl-3-phenylacetyl-2-oxazolidinone.

Workup

  1. temperatureCool in a dry-ice acetone bath
  2. waitAfter 20 minutes
  3. waitAfter 2 hours
  4. customquench the reaction mixture
  5. additionby the addition of a saturated aqueous sodium bicarbonate solution
  6. customSeparate the layers
  7. extractionextract the aqueous layer with diethyl ether
  8. dry with materialdry over Na2SO4
  9. filtrationfilter
  10. customevaporate in vacuo
  11. customto give a residue
  12. additioncontaining fractions
  13. customevaporate

Sources & evidence

ORD record
ord-0ae8dbd2e3fe4cf39f65ab0128d14b97
Source dataset
uspto-grants-1999_08
Patent number
US05932571

Reaction notes

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