Sodium hydride → HCID 14306107, compound

HRID 232198Notes

Reaction equation

HRID 232198 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

In 5 ml of N,N-dimethylformamide solution was dissoved 838 mg of 2-benzyloxycarbonylamino-5-oxo-2-tetrahydrofurancarboxylic acid. To the solution was added 120 mg of sodium hydride (60% oil). To the mixture was added 648 mg of 4-nitrobenzyl bromide, followed by stirring at room temperature for 2.5 hours. To the reaction solution was added a saturated aqueous solution of sodium hydrogen carbonate, which was subjected to extraction with ethyl acetate. The aqueous layer was then dried (MgSO4), followed by removal of the solvent by evaporation. The residue was subjected to a silica gel column chromatography, followed by elution with hexane-ethyl acetate (1:1) to give 687 mg of 4-nitrobenzyl 2-benzyloxycarbonylamino-5-oxo-2-tetrahydrofurancarboxylate as colorless crystals, m.p. 127-127.5° C.

Workup

  1. extractionwas subjected to extraction with ethyl acetate
  2. dry with materialThe aqueous layer was then dried (MgSO4)
  3. customfollowed by removal of the solvent by evaporation
  4. washfollowed by elution with hexane-ethyl acetate (1:1)

Sources & evidence

ORD record
ord-2149e193c70d4fddb2ff9c5348c4c8f8
Source dataset
uspto-grants-1989_07
Patent number
US04851422

Reaction notes

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