Formic Acid → HCID 86649142, compound

HRID 1408285Notes

Reaction equation

HRID 1408285 reaction equation
[C:1](OC(=O)C)(=[O:3])C.C([O:11][CH2:12][CH2:13][NH:14][C:15]([C:17]1[C:18]([I:40])=[C:19]([C:34]([I:39])=[C:35]([NH2:38])[C:36]=1[I:37])[C:20]([NH:22][CH:23]([CH2:29]CC([O-])=O)[CH2:24]CC([O-])=O)=[O:21])=[O:16])(=O)C.[OH-:41].[Na+].C(O)=[O:44]>>[OH:41][CH2:29][CH:23]([NH:22][C:20](=[O:21])[C:19]1[C:34]([I:39])=[C:35]([NH:38][CH:1]=[O:3])[C:36]([I:37])=[C:17]([C:15]([NH:14][CH2:13][CH2:12][OH:11])=[O:16])[C:18]=1[I:40])[CH2:24][OH:44]

Participants

5

Reactant 4

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 14798Sodium Hydroxide2×HCID 86649143HCID 86649143, compound

Product 1

HCID 86649142HCID 86649142, compoundYield 82.9%

Procedure

Acetic anhydride (19.47 ml, 20.6 mmol) was added to formic acid (100 ml) under ice cooling keeping the temperature below 5° C. After complete addition the cooling-bath was removed and the temperature was allowed to reach 10° C. The ice cooling was continued and 2-(3-(2-acetoxyethylcarbamoyl)-5-amino-2,4,6-triiodobenzamido)propane-1,3-diyldiacetate (33 g, 41.2 mmol) was then added in portions over 3 minutes. The mixture was left to stir overnight and then evaporated in vacuo to afford a white foam to which methanol (100 ml) and water (100 ml) was added. While stirring, 10N NaOH was added drop wise until a clear solution was obtained. Drop wise addition of 10N NaOH was continued until pH stabilized at 11.60. Methanol was removed from the mixture by evaporation in vacuo and the solution was acidified to pH 2.7 with 18.6% HCl. The mixture was placed in a refrigerator overnight and the product, precipitated from the solution was collected, washed with water and dried at 60° C. to afford 24 g of N1-(1,3-dihydroxypropan-2-yl)-5-formamido-N3-(2-hydroxyethyl)-2,4,6-triiodoisophthalamide (82.9% yield).

Workup

  1. customthe temperature below 5° C
  2. additionAfter complete addition the cooling-bath
  3. customwas removed
  4. customto reach 10° C
  5. waitThe mixture was left
  6. customevaporated in vacuo
  7. customto afford a white foam to which methanol (100 ml) and water (100 ml)
  8. additionwas added
  9. stirringWhile stirring
  10. customwas obtained
  11. customMethanol was removed from the mixture by evaporation in vacuo
  12. customwas placed in a refrigerator overnight
  13. customthe product, precipitated from the solution
  14. customwas collected
  15. washwashed with water
  16. customdried at 60° C.

Sources & evidence

ORD record
ord-861ccda341a441b9a271bc45c0b0e126
Source dataset
uspto-grants-2014_12
Patent number
US08920780B2

Reaction notes

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