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

HRID 429480Notes

Reaction equation

HRID 429480 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-26e9eb1506c448fc933b0a08c6114af0
Source dataset
uspto-grants-2001_11
Patent number
US06316445B1

Reaction notes

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