Sodium Bicarbonate → 5-(3-Acetoxy-2,2-diacetoxymethyl-propionylamino)-3-acetoxymethyl-N-(2,3-diacetoxypropyl)-2,4,6-triiodobenzamide

HRID 383038Notes

Reaction equation

HRID 383038 reaction equation
[NH2:1][C:2]1[C:3]([I:29])=[C:4]([CH2:24][O:25][C:26](=[O:28])[CH3:27])[C:5]([I:23])=[C:6]([C:21]=1[I:22])[C:7]([NH:9][CH2:10][CH:11]([O:17][C:18](=[O:20])[CH3:19])[CH2:12][O:13][C:14](=[O:16])[CH3:15])=[O:8].[C:30]([O:33][CH2:34][C:35]([CH2:44][O:45][C:46](=[O:48])[CH3:47])([CH2:39][O:40][C:41](=[O:43])[CH3:42])[C:36](Cl)=[O:37])(=[O:32])[CH3:31].C(=O)([O-])O.[Na+]>CC(N(C)C)=O>[C:41]([O:40][CH2:39][C:35]([CH2:44][O:45][C:46](=[O:48])[CH3:47])([CH2:34][O:33][C:30](=[O:32])[CH3:31])[C:36]([NH:1][C:2]1[C:3]([I:29])=[C:4]([CH2:24][O:25][C:26](=[O:28])[CH3:27])[C:5]([I:23])=[C:6]([C:21]=1[I:22])[C:7]([NH:9][CH2:10][CH:11]([O:17][C:18](=[O:20])[CH3:19])[CH2:12][O:13][C:14](=[O:16])[CH3:15])=[O:8])=[O:37])(=[O:43])[CH3:42]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 184291303-Acetoxymethyl-5-(2,3-diacetoxypropylaminocarbonyl)-2,4,6-triiodoanilineHCID 85706307HCID 85706307, compound

Product 1

HCID 881689485-(3-Acetoxy-2,2-diacetoxymethyl-propionylamino)-3-acetoxymethyl-N-(2,3-diacetoxypropyl)-2,4,6-triiodobenzamide

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
60 °C

Procedure

5-Amino-3-acetoxymethyl-N-(2,3-diacetoxypropyl)-2,4,6-triiodobenzamide (1.05 g, 1.43 mmol) was dissolved in dimethylacetamide (2 ml) and added to trisacetoxymethylacetyl chloride (2.17 g, 7.4 mmol). The mixture was stirred at 60° C. for 5 days, and after cooling the mixture was added to an aqueous solution of sodium hydrogen carbonate (60 ml, 2%). The precipitate formed was filtered off and dissolved in chloroform (90 ml). The organic phase was washed with water (4×40 ml), dried (Na2SO4), and the solvent evaporated. A semisolid residue (1.16 g) was left, which according to MS analysis consisted of the two compounds: 5-(3-Acetoxy-2,2-diacetoxymethyl-propionylamino)-3-acetoxymethyl-N-(2,3-diacetoxypropyl)-2,4,6-triiodobenzamide with MS (ESP, m/e): 1002 ([M]+, 100%) and 5-acetamido-3-acetoxymethyl-N-(2,3-diacetoxypropyl)-2,4,6-triiodobenzamide with

Workup

  1. temperatureafter cooling the mixture
  2. customThe precipitate formed
  3. filtrationwas filtered off
  4. dissolutiondissolved in chloroform (90 ml)
  5. washThe organic phase was washed with water (4×40 ml)
  6. dry with materialdried (Na2SO4)
  7. customthe solvent evaporated
  8. waitA semisolid residue (1.16 g) was left

Sources & evidence

ORD record
ord-7df377fd6b1342a9adafba3c18a1ac45
Source dataset
uspto-grants-2001_10
Patent number
US06310243B1

Reaction notes

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