Bicarbonate Ion → HCID 45122267, compound

Participants

Reaction Steps

A mixture of 7.2 g of (3,5-difluorophenyl)acetamide 1 and 4.6 g of glyoxylic acid hydrate in 75 mL of acetone was refluxed 24 hours. The solvent was evaporated and the residue was dissolved in 300 mL of ethyl acetate. This solution washed with 150 mL of distilled water. The aqueous phase was discarded. The organic phase was extracted with a solution prepared by diluting 50 mL of a saturated aqueous solution of sodium bicarbonate with 150 mL of distilled water. The organic phase was discarded and the aqueous bicarbonate solution was acidified with 80 mL of 1 N aqueous sodium bisulfate solution. The acidified solution was extracted with three successive 125 mL portions of ethyl acetate. The combined organic extracts were washed with brine and then dried over magnesium sulfate. The solution was filtered and the solvent was evaporated to yield 2-[(3,5-difluorophenyl)acetylamino]-2-hydroxyacetic acid as 5.2 g of a white solid. 1H-NMR (DMSO-d6): δ 8.95 (d, J=8 Hz, 1H), 7.15-6.90 (m, 3H), 5.37 (d, J=8 Hz, 1H), 3.50 (s, 2H). 13C-NMR (DMSO-d66) δ 171.5, 169.4, 162.4 (dd, JC-F=13, 244 Hz), 140.6 (t, JC-F=10 Hz), 112.6 (dd, JC-F=8, 17 Hz), 71.5, 41.7. MS (CI+): m/z 246. EA Calc'd for C10H9F2NO4: C, 48.98; H, 3.71; N, 5.71. Found: C, 49.02; H, 3.72; N, 5.51.

Provenance & Evidence