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

HRID 232197Notes

Reaction equation

HRID 232197 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-tetrahydrofurancarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 100 ml of N,N-dimethylformamide was dissolved 27.93 g of 2-benzyloxycarbonylamino-5-oxo-2-tetrahydrofurancarboxylic acid obtained 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 further added 28.4 of methyl iodide, and the reaction was allowed to proceed at room temperature for 4 hours. The reaction mixture was supplemented with 14.2 g of methyl iodide, which was stirred for further 3 hours. The reaction solution was poured into water, which was subjected to extraction with ethyl acetate. The organic layer was washed with sodium hydrogen carbonate and a saturated saline solution, successively, followed by drying (MgSO4). The solvent was evaporated off, and the crystals which separated out 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. customobtained by the method
  2. extractionwas subjected to extraction with ethyl acetate
  3. washThe organic layer was washed with sodium hydrogen carbonate
  4. dry with materialby drying (MgSO4)
  5. customThe solvent was evaporated off
  6. customthe crystals which separated out
  7. filtrationwere collected by filtration
  8. washby washing with ether

Sources & evidence

ORD record
ord-ecdd1b612d6341dd8edc4936673d0074
Source dataset
uspto-grants-1989_07
Patent number
US04851422

Reaction notes

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