Sodium Bicarbonate → (S)-4-benzyl-3-(3,4-dichlorophenyl)acetyl-2-oxazolidinone

HRID 429466Notes

Reaction equation

HRID 429466 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.[Cl:19][C:20]1[CH:21]=[C:22]([CH2:27][C:28](Cl)=[O:29])[CH:23]=[CH:24][C:25]=1[Cl:26].C(=O)(O)[O-].[Na+].C([O-])(=O)C.CCCCCC>O1CCCC1.C(OCC)C.C(OCC)C.CCCCCC.C(OCC)(=O)C.CCCCCC>[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:28](=[O:29])[CH2:27][C:22]1[CH:23]=[CH:24][C:25]([Cl:26])=[C:20]([Cl:19])[CH:21]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

10

Reactant 5

HCID 516892Sodium BicarbonateHCID 736225(S)-4-Benzyl-2-oxazolidinoneHCID 27581492-(3,4-Dichlorophenyl)acetyl chlorideHCID 22139250Acetate hexaneHCID 178418339Butyllithium

Product 1

HCID 69777551(S)-4-benzyl-3-(3,4-dichlorophenyl)acetyl-2-oxazolidinone

Reagents, catalysts & solvents 4

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×HCID 21226206Ethyl acetate hexaneSolvent6×HCID 21584099Diethylether hexaneSolvent

Procedure

Combine (S)-4-benzyl-2-oxazolidinone (2.6 g, 34 mmol) and tetrahydrofuran (80 mL). Cool in a dry-ice/acetone bath. Add dropwise a solution of n-butyl lithium (13.5 mL, 2.5 M, 27 mmol). After 15 minutes, slowly add a solution of 3,4-dichlorophenylacetyl chloride (9.4 g, 44 mmol) in tetrahydrofuran (20 mL). After 20 minutes, warm to ambient temperature. After 2 hours, dilute the reaction mixture with diethyl ether and add a saturated aqueous sodium bicarbonate solution. Separate the layers and extract the organic layer with a saturated ammonium chloride solution and then water. Dry over MgSO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting sequentially with 5% ethyl acetate/hexane, 10% ethyl acetate/hexane, and 15% ethyl acetate/hexane. Combine the product containing fraction to give a residue. Rechromatograph the residue on silica gel eluting sequentially with 5% ethyl is acetate/hexane, 10% ethyl acetate/hexane, 15% ethyl acetate/hexane, and 20% ethyl acetate/hexane to give a residue. Recrytallize from diethyl ether/hexane to give (S)-4-benzyl-3-(3,4-dichlorophenyl)acetyl-2-oxazolidinone: mp; 70.5-71.5° C. Rf=0.75 (silica gel, 50% ethyl acetate/hexane).

Workup

  1. temperatureCool in a dry-ice/acetone bath
  2. waitAfter 20 minutes
  3. waitAfter 2 hours
  4. customSeparate the layers
  5. extractionextract the organic layer with a saturated ammonium chloride solution
  6. dry with materialDry over MgSO4
  7. filtrationfilter
  8. customevaporate in vacuo
  9. customto give a residue
  10. additioncontaining fraction
  11. customto give a residue
  12. customto give a residue

Sources & evidence

ORD record
ord-feda8ecde3934c48a7c05626dd8cb140
Source dataset
uspto-grants-2001_11
Patent number
US06316445B1

Reaction notes

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