D-Glutamic Acid → (R)-5-oxo-2-tetrahydrofurancarboxylic acid
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]1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To a mixture of D-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 (12.63 g, 57%). M.P. 71-73° C.; 1H NMR (400 MHz, CD3OD) δ 4.20 (m, 1H, CHO), 1.8-2.3 (m, 4H, CH2CH2).