L-Glutamic Acid → (2S)-5-oxooxolane-2-carboxylic acid

HRID 1641421Notes

Reaction equation

HRID 1641421 reaction equation
N[C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5]([OH:7])=[O:6].N([O-])=O.[Na+]>O.Cl>[O:9]=[C:8]1[O:10][C@H:4]([C:5]([OH:7])=[O:6])[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 33032L-Glutamic AcidHCID 23668193Sodium Nitrite

Product 1

HCID 636468(2S)-5-oxooxolane-2-carboxylic acidYield 59.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Procedure

To a mixture of L-glutamic acid (1, 25 g, 170 mmol) in water (67 mL) and conc. HCl (35 mL) at 0° C. with stirring was added a solution of NaNO2 (17.5 g, 253.6 mmol) in water (37.5 mL) over a period of 4 h, and then the resulting clear solution was stirred at room temperature overnight. After removal of the solvent by evaporation in vacuo, the residue was treated with EtOAC (80 mL) and filtered. The filtrate was dried over Na2SO4, and concentrated. The residue, after crystallization from EtOAc/benzene/hexane, afforded the title compound 2 as a white crystalline solid (13.12 g, 59%). M.P. 71-73° C.; 1H NMR (400 MHz, CD3OD) δ 4.20 (m, 1H, CHO), 1.8-2.3 (m, 4H, CH2CH2).

Workup

  1. stirringthe resulting clear solution was stirred at room temperature overnight
  2. customAfter removal of the solvent
  3. customby evaporation in vacuo
  4. additionthe residue was treated with EtOAC (80 mL)
  5. filtrationfiltered
  6. dry with materialThe filtrate was dried over Na2SO4
  7. concentrationconcentrated
  8. customThe residue, after crystallization from EtOAc/benzene/hexane

Sources & evidence

ORD record
ord-dfa947f2d1df4f50893d3258bc13302f
Source dataset
uspto-grants-2012_02
Patent number
US08114997B2

Reaction notes

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