D-Glutamic Acid → (R)-5-oxo-2-tetrahydrofurancarboxylic acid

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).

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

ORD record

ord-bc4cc98b77dc4eb39a46e3f8a01cd65c

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07772208B2