(S)-4-Benzyl-2-oxazolidinone → (S)-4-Benzyl-3-(2-(4-fluorophenyl)acetyl)oxazolidin-2-one

HRID 429473Notes

Reaction equation

HRID 429473 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.[F:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][C:27](Cl)=[O:28])=[CH:22][CH:21]=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:27](=[O:28])[CH2:26][C:23]1[CH:24]=[CH:25][C:20]([F:19])=[CH:21][CH:22]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 736225(S)-4-Benzyl-2-oxazolidinoneHCID 37449884-Fluorophenylacetyl chlorideHCID 21226206Ethyl acetate hexaneHCID 178418339Butyllithium

Product 1

HCID 15536019(S)-4-Benzyl-3-(2-(4-fluorophenyl)acetyl)oxazolidin-2-one

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 4-fluorophenylacetyl chloride (22.3 g, 129 mmol) in tetrahydrofuran (50 mL). 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 wit 15% ethyl acetate/hexane. Combine the product containing fractions, evaporate, and recrytallize from diethyl ether/hexane to give (S)-4-benzyl-3-(4-fluorophenyl)acetyl-2-oxazolidinone.

Workup

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

Sources & evidence

ORD record
ord-be68e293be824831aec232ac0fcbe26f
Source dataset
uspto-grants-2001_11
Patent number
US06316445B1

Reaction notes

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