Diethyl Oxalate → HCID 54692482, compound

HRID 2109825Notes

Reaction equation

HRID 2109825 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:6](=[O:17])[CH2:5]1)(=[O:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C1COCC1.[C:33](OCC)(=[O:39])[C:34](OCC)=[O:35]>CN(C=O)C>[CH2:10]([N:7]1[CH2:8][CH2:9][N:4]2[C:1](=[O:3])[CH:2]=[C:33]([OH:39])[C:34]([OH:35])=[C:5]2[C:6]1=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 7268Diethyl OxalateHCID 8028Tetrahydrofuran2×HCID 2733832Lithium Hexamethyldisilazide2×HCID 12744518HCID 12744518, compound

Product 1

HCID 54692482HCID 54692482, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a cold (0° C.) solution of 4-acetyl-1-benzylpiperazin-2-one (0.49 g, 2.1 mmol) in DMF (10 mL) under an atmosphere of nitrogen, a solution of lithium bis(trimethylsilyl)amide in THF (2.5 mL, 2.5 mmol) was added and stirred at the temperature for 30 min. The resultant solution was treated with diethyl oxalate (0.43 mL, 3.1 mmol), and stirred at room temperature overnight. The resultant mixture was then treated with additional lithium bis(trimethylsilyl)amide in THF (10 mL, 10 mmol) and stirred at room temperature for 6 h. The product mixture was concentrated under vacuum, and the residue partitioned between aqueous HCl and ethyl acetate. The organic extract was dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum. The residue was subjected to HPLC purification on C-18 stationary phase eluted with water/acetonitrile/TFA mobile phase. Collection and lyophilization of appropriate fractions provided the title compound as white solid.

Workup

  1. stirringstirred at room temperature overnight
  2. stirringstirred at room temperature for 6 h
  3. concentrationThe product mixture was concentrated under vacuum
  4. customthe residue partitioned between aqueous HCl and ethyl acetate
  5. extractionThe organic extract
  6. dry with materialwas dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customThe residue was subjected to HPLC purification on C-18 stationary phase
  10. washeluted with water/acetonitrile/TFA mobile phase
  11. customCollection and lyophilization of appropriate fractions

Sources & evidence

ORD record
ord-bcca865512624d7494ae98795c8526be
Source dataset
uspto-grants-2009_04
Patent number
US07517532B2

Reaction notes

Loading…