Benzyl Chloride → HCID 19969576, compound

HRID 974857Notes

Reaction equation

HRID 974857 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7](Cl)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:15]([O:17][C:18]([CH:20]1[NH:25][C:24](=[O:26])[CH:23]([CH2:27][CH:28]([CH3:30])[CH3:29])[N:22]([OH:31])[C:21]1=[O:32])=[O:19])[CH3:16]>CN(C)C=O.C(OCC)(=O)C>[CH2:7]([C:20]1([C:18]([O:17][CH2:15][CH3:16])=[O:19])[NH:25][C:24](=[O:26])[CH:23]([CH2:27][CH:28]([CH3:29])[CH3:30])[N:22]([O:31][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:21]1=[O:32])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 19969538HCID 19969538, compound

Product 1

HCID 19969576HCID 19969576, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

7.60 g of potassium carbonate and 6.3 ml of benzyl chloride were added to 100 ml of a solution of 9.57 g of 3-ethoxycarbonyl-1-hydroxy-6-isobutylpiperazine-2,5-dione in anhydrous N,N-dimethylformamide, on ice-cooling. The mixture was stirred at room temperature for 16 hours. The reaction mixture was diluted with 450 ml of ethyl acetate, then washed three times with an aqueous solution saturated with sodium chloride, and dried with anhydrous magnesium sulfate. The resulting solution was subjected to distillation to remove the solvent. The residue was allowed to stand. The resulting crystals were collected by filtration and washed with methanol to obtain 4.51 g of (3RS,6SR)-3-benzyl-1-benzyloxy-3-ethoxycarbonyl-6-isobutylpiperazine-2,5-dione as colorless columnar crystals.

Workup

  1. temperaturecooling
  2. washwashed three times with an aqueous solution saturated with sodium chloride
  3. dry with materialdried with anhydrous magnesium sulfate
  4. distillationThe resulting solution was subjected to distillation
  5. customto remove the solvent
  6. filtrationThe resulting crystals were collected by filtration
  7. washwashed with methanol

Sources & evidence

ORD record
ord-04f906b2979443e5bafef526b326b11e
Source dataset
uspto-grants-1997_03
Patent number
US05607934

Reaction notes

Loading…