4-Nitrobenzyl bromide → HCID 19844030, compound

HRID 2352285Notes

Reaction equation

HRID 2352285 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1([C:18]([OH:20])=[O:19])[CH2:16][CH2:15][C:14](=[O:17])[O:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:21]([C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Br)=[CH:26][CH:25]=1)([O-:23])=[O:22].C(=O)(O)[O-:33].[Na+]>CN(C)C=O>[C:1]([O:8][C:9]([NH:11][C:12]1([C:18]([O:20][CH2:28][C:27]2[CH:30]=[CH:31][C:24]([N+:21]([O-:23])=[O:22])=[CH:25][CH:26]=2)=[O:19])[CH2:16][CH2:15][C:14](=[O:17])[O:13]1)=[O:10])(=[O:33])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 660114-Nitrobenzyl bromideHCID 516892Sodium BicarbonateHCID 31063662-(((Benzyloxy)carbonyl)amino)-5-oxotetrahydrofuran-2-carboxylic acid

Product 1

HCID 19844030HCID 19844030, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 838 mg 2-benzyloxycarbonylamino-5-oxo-2tetrahydrofurancarboxylic acid in 5 ml of dimethylformamide 120 mg sodium hydride (60% dispersion in mineral oil) was added, while stirring and ice-cooling the solution. 648 mg 4-nitrobenzyl bromide was then added, and the mixture was stirred at room temperature for 2.5 hours. To the reaction mixture a saturated aqueous solution of sodium bicarbonate was added, then the resulting mixture was extracted with ethyl acetate. The organic layer, after washing with brine, was dried (MgSO4), and the solvent was distilled off. The resulting residue was eluted with hexane-ethyl acetate (1:1) via column chromatography using silica gel. The eluted fraction containing the desired product was collected and concentrated under reduced pressure to yield 687 mg 4-nitrobenzyl 2-benzoyloxycarbonylamino-5-oxo-2-tetrahydrofurancarboxylate in the form of a colorless crystal.

Workup

  1. temperatureice-cooling the solution
  2. stirringthe mixture was stirred at room temperature for 2.5 hours
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. washThe organic layer, after washing with brine
  5. dry with materialwas dried (MgSO4)
  6. distillationthe solvent was distilled off
  7. washThe resulting residue was eluted with hexane-ethyl acetate (1:1) via column chromatography
  8. additionThe eluted fraction containing the desired product
  9. customwas collected
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-434f221304984eeda363718d99bebaf7
Source dataset
uspto-grants-1989_10
Patent number
US04876251

Reaction notes

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