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

HRID 329536Notes

Reaction equation

HRID 329536 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+].[CH3:23]I.O>CN(C)C=O>[CH2:1]([O:8][C:9]([NH:11][C:12]1([C:18]([O:20][CH3:23])=[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 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

In 100 ml of dimethylformamide was dissolved 27.93 g of 2-benzyloxycarbonylamino-5-oxo-2-tetrahydrofurancarboxylic acid prepared by the method described in Journal of Organic Chemistry, 6, 878 (1941). To the solution was added 4.0 g of sodium hydride (60% oil), to which was then added 28.4 g of methyl iodide, followed by allowing the reaction to proceed at room temperature for 4 hours. To the resultant was added 28.4 g of methyl iodide, and the mixture was stirred for further 3 hours. The reaction mixture was added to water, which was subjected to extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous saline solution, successively, then dried (MgSO4). The solvent was distilled off, and precipitating crystals were collected by filtration, followed by washing with ether to give 27.25 g of methyl 2-benzyloxycarbonylamino-5-oxo-2-tetrahydrofurancarboxylate as colorless crystals, m.p. 134°-134.5° C.

Workup

  1. customprepared by the method
  2. customthe reaction
  3. extractionwas subjected to extraction with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate
  5. dry with materiala saturated aqueous saline solution, successively, then dried (MgSO4)
  6. distillationThe solvent was distilled off
  7. customprecipitating crystals
  8. filtrationwere collected by filtration
  9. washby washing with ether

Sources & evidence

ORD record
ord-2e40db9fd848438ea550803662dca851
Source dataset
uspto-grants-1990_01
Patent number
US04891427

Reaction notes

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