Bicarbonate Ion → HCID 45122267, compound

HRID 2356849Notes

Reaction equation

HRID 2356849 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([NH2:12])=[O:11])[CH:5]=[C:6]([F:8])[CH:7]=1.O.[C:14]([OH:18])(=[O:17])[CH:15]=[O:16].C(=O)(O)[O-].[Na+].C(=O)(O)[O-].S(=O)(=O)(O)[O-].[Na+]>CC(C)=O.O>[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([NH:12][CH:15]([OH:16])[C:14]([OH:18])=[O:17])=[O:11])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

8

Reactant 5

HCID 769Bicarbonate IonHCID 516892Sodium BicarbonateHCID 516919Sodium BisulfateHCID 15620607Glyoxylic acid, monohydrateHCID 21644871HCID 21644871, compound

Product 1

HCID 45122267HCID 45122267, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

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.

Workup

  1. temperaturewas refluxed 24 hours
  2. customThe solvent was evaporated
  3. dissolutionthe residue was dissolved in 300 mL of ethyl acetate
  4. washThis solution washed with 150 mL of distilled water
  5. extractionThe organic phase was extracted with a solution
  6. customprepared
  7. extractionThe acidified solution was extracted with three successive 125 mL portions of ethyl acetate
  8. washThe combined organic extracts were washed with brine
  9. dry with materialdried over magnesium sulfate
  10. filtrationThe solution was filtered
  11. customthe solvent was evaporated

Sources & evidence

ORD record
ord-ccabaf07cafd4a469b02ef3a0ad7ab9c
Source dataset
uspto-grants-2010_07
Patent number
US07759382B2

Reaction notes

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