Water → Methyl 2-benzyloxycarbonylamino-5-oxo-2-tetrahydrofurancarboxylate

HRID 2352284Notes

Reaction equation

HRID 2352284 reaction equation
[H-].[Na+].[CH2:3]([O:10][C:11]([NH:13][C:14]1([C:20]([OH:22])=[O:21])[CH2:18][CH2:17][C:16](=[O:19])[O:15]1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:23]I.O>CN(C)C=O>[CH2:3]([O:10][C:11]([NH:13][C:14]1([C:20]([O:22][CH3:23])=[O:21])[CH2:18][CH2:17][C:16](=[O:19])[O:15]1)=[O:12])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodide2×HCID 24758Sodium hydrideHCID 31063662-(((Benzyloxy)carbonyl)amino)-5-oxotetrahydrofuran-2-carboxylic acid

Product 1

HCID 13995237Methyl 2-benzyloxycarbonylamino-5-oxo-2-tetrahydrofurancarboxylateYield 92.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4.0 g sodium hydride (60% dispersion in mineral oil) was added to a solution of 27.93 g of 2-benzyloxycarbonylamino-5-oxo-2-tetrahydrofurancarboxylic acid obtained via the method described in the Journal of Organic Chemistry, 6, 878 (1941) in 100 ml dimethylformamide while stirring and ice-cooling the solution. 28.4 g methyl iodide was then added, and the reaction mixture was stirred at room temperature for 4 hours. 14.2 g methyl iodide was further added, and the mixture was stirred for 3 more hours. The mixture was poured into water and extracted with ethyl acetate. The organic layer was successively washed with aqueous sodium bicarbonate and brine, and thereafter it was dried (over MgSO4). The solvent was distilled off, and the precipitating crystal was collected by filtration and washed with ether to yield 27.25 g methyl 2-benzyloxycarbonylamino-5-oxo-2-tetrahydrofurancarboxylate in the form of a colorless crystal.

Workup

  1. customobtained via the method
  2. temperatureice-cooling the solution
  3. stirringthe reaction mixture was stirred at room temperature for 4 hours
  4. stirringthe mixture was stirred for 3 more hours
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was successively washed with aqueous sodium bicarbonate and brine
  7. dry with materialit was dried (over MgSO4)
  8. distillationThe solvent was distilled off
  9. filtrationthe precipitating crystal was collected by filtration
  10. washwashed with ether

Sources & evidence

ORD record
ord-c992b1045ccf4be79d62a1f04979c4cc
Source dataset
uspto-grants-1989_10
Patent number
US04876251

Reaction notes

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