Sodium hydride → HCID 14306107, compound

HRID 1032033Notes

Reaction equation

HRID 1032033 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.[H-].[Na+].[N+:23]([C:26]1[CH:33]=[CH:32][C:29]([CH2:30]Br)=[CH:28][CH:27]=1)([O-:25])=[O:24].C(=O)([O-])O.[Na+]>CN(C)C=O>[CH2:1]([O:8][C:9]([NH:11][C:12]1([C:18]([O:20][CH2:30][C:29]2[CH:32]=[CH:33][C:26]([N+:23]([O-:25])=[O:24])=[CH:27][CH:28]=2)=[O:19])[CH2:16][CH2:15][C:14](=[O:17])[O:13]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 660114-Nitrobenzyl bromideHCID 516892Sodium BicarbonateHCID 31063662-(((Benzyloxy)carbonyl)amino)-5-oxotetrahydrofuran-2-carboxylic acid

Product 1

HCID 14306107HCID 14306107, compoundYield 55.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 838 mg of 2-benzyloxycarbonylamino-5-oxo-2-tetrahydrofurancarboxylic acid in 5 ml of dimethylformamide was added 120 mg of sodium hydride (60% oil) while stirring under ice-cooling. To the mixture was then added 648 mg of 4-nitrobenzyl bromide, followed by stirring at room temperature for 2.5 hours. To the reaction mixture was added a saturated aqueous solution of sodium hydrogencarbonate, which was subjected to extraction with ethyl acetate. The organic layer was washed with a saturated aqueous saline solution and then dried (MgSO4), followed by distilling off the solvent. The residue was subjected to a silica gel column chromatography, eluting with hexane ethyl acetate (1:1). Fractions containing the end product were combined and concentrated under reduced pressure to give 687 mg of 4-nitrobenzyl 2-benzyloxycarbonylamino-5-oxo-2-tetrahydrofurancarboxylate as colorless crystals, m.p.127°-127.5° C. IRνmaxKBr cm-1 : 3310, 1780, 1759, 1728, 1520, 1345, 1185, 1042

Workup

  1. temperaturecooling
  2. stirringby stirring at room temperature for 2.5 hours
  3. extractionwas subjected to extraction with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous saline solution
  5. dry with materialdried (MgSO4)
  6. distillationby distilling off the solvent
  7. washeluting with hexane ethyl acetate (1:1)
  8. additionFractions containing the end product
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3fd58ca367634076a93f941f1b052bd4
Source dataset
uspto-grants-1990_09
Patent number
US04956358

Reaction notes

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