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

HRID 2213066Notes

Reaction equation

HRID 2213066 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) δ4.20 (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-bdf4fe1de74d4c0fb08b8bf997f360e0
Source dataset
uspto-grants-2006_09
Patent number
US07105527B2

Reaction notes

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