Glyoxylic Acid → HCID 15236522, compound

HRID 861705Notes

Reaction equation

HRID 861705 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[C:12]([OH:16])(=[O:15])[CH:13]=O.[CH2:17]([NH:24][CH2:25][C:26]([OH:28])=[O:27])[CH2:18][NH:19][CH2:20][C:21]([OH:23])=[O:22].[OH-].[Na+]>CO.O>[C:26]([CH2:25][N:24]([CH2:13][C:12]([OH:16])=[O:15])[CH2:17][CH2:18][NH:19][CH:20]([C:9]1[CH:10]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[CH:6]=[CH:7][C:8]=1[OH:11])[C:21]([OH:23])=[O:22])([OH:28])=[O:27]

Participants

7

Reactant 4

HCID 760Glyoxylic AcidHCID 1983AcetaminophenHCID 14798Sodium HydroxideHCID 61975Ethylenediaminediacetic acid

Product 1

HCID 15236522HCID 15236522, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Deionized water (10.3 g), 98% 4-acetamidophenol (15.1 g 0.1 mole), 50% aqueous glyoxylic acid (14.8 g, 0.1 mole), and methanol (50.5 g) were added to a beaker and mixed using a magnetic stirrer bar. Unsymmetrical ethylenediaminediacetic acid (19.5 g), prepared by the procedure of Example A, was added and the mix cooled in an ice-water bath. The pH of the mix was adjusted, while stirring, to approximately 8.0 with 50% sodium hydroxide solution. The temperature of the mix was maintained at less than 20° C. during the caustic addition. The ice-water bath was removed and the mix adjusted to pH 8.7 and stirred at 25°-32° C. for approximately 2 hours. The mix was transferred to a round-bottom reaction flask equipped with a water-cooled reflux condenser, magnetic stirrer bar, thermometer, and a heating mantle. The mix was heated, with stirring, at 70° C. for 8 hours and then cooled and filtered using a medium glass frit funnel and vacuum. The solids were allowed to dry by exposure to air for 7 hours and then placed in a vacuum oven and dried at 55°-60° C. for several hours. Approximately 29.6 g of solids were collected. The material was then agitated with approximately 300 g of acetone and filtered using a medium glass frit funnel and house vacuum. The solids were washed once again with an additional 300 g of acetone, air dried and then placed in a vacuum oven for one hour at 55°-60° C. Approximately 26.7 g of 2-[(2-{[bis(carboxymethyl)]-amino}ethyl)amino]-2-(5-acetamido-2-hydroxyphenyl)ethanoic acid, sodium salt were collected. These solids and 180 g of deionized water were placed in a beaker and stirred with a magnetic stirrer bar. The pH was adjusted to 2.2 with concentrated hydrochloric acid at which point the acid form of the product began to precipitate from solution. The product was collected by filtration and washed with approximately 150 g of deionized water. The product, 2-[(2-{[bis(carboxymethyl)]amino}ethyl)amino]-2-(5-acetamido-2-hydroxyphenyl)ethanoic acid was dried in a vacuum oven at 55°-60° C. for several hours. Approximately 14.2 g of product were obtained. Proton NMR verified the structure of the product. (See Table I.)

Workup

  1. additionmixed
  2. additionwas added
  3. temperaturethe mix cooled in an ice-water bath
  4. temperatureThe temperature of the mix was maintained at less than 20° C. during the caustic addition
  5. customThe ice-water bath was removed
  6. customThe mix was transferred to a round-bottom reaction flask
  7. customequipped with a water-
  8. temperaturecooled
  9. temperaturereflux condenser, magnetic stirrer bar
  10. temperatureThe mix was heated
  11. stirringwith stirring, at 70° C. for 8 hours
  12. temperaturecooled
  13. filtrationfiltered
  14. customto dry by exposure to air for 7 hours
  15. customdried at 55°-60° C. for several hours
  16. customApproximately 29.6 g of solids were collected
  17. stirringThe material was then agitated with approximately 300 g of acetone
  18. filtrationfiltered
  19. washThe solids were washed once again with an additional 300 g of acetone, air
  20. customdried
  21. waitplaced in a vacuum oven for one hour at 55°-60° C
  22. customApproximately 26.7 g of 2-[(2-{[bis(carboxymethyl)]-amino}ethyl)amino]-2-(5-acetamido-2-hydroxyphenyl)ethanoic acid, sodium salt were collected
  23. stirringstirred with a magnetic stirrer bar
  24. customto precipitate from solution
  25. filtrationThe product was collected by filtration
  26. washwashed with approximately 150 g of deionized water
  27. dry with materialThe product, 2-[(2-{[bis(carboxymethyl)]amino}ethyl)amino]-2-(5-acetamido-2-hydroxyphenyl)ethanoic acid was dried in a vacuum oven at 55°-60° C. for several hours

Sources & evidence

ORD record
ord-ae7bc89f147343a5b6254066d89944e2
Source dataset
uspto-grants-1998_02
Patent number
US05714631

Reaction notes

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