Sodium Bicarbonate → HCID 18429174, compound

HRID 1280181Notes

Reaction equation

HRID 1280181 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][CH:34]([CH:38]([O:44][C:45](=[O:47])[CH3:46])[CH2:39][O:40][C:41](=[O:43])[CH3:42])[C:35](Br)=[O:36])(=[O:32])[CH3:31].C([O-])(O)=O.[Na+]>CN(C)C(=O)C>[C:30]([O:33][CH:34]([CH:38]([O:44][C:45](=[O:47])[CH3:46])[CH2:39][O:40][C:41](=[O:43])[CH3:42])[C:35]([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:36])(=[O:32])[CH3:31]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 184291303-Acetoxymethyl-5-(2,3-diacetoxypropylaminocarbonyl)-2,4,6-triiodoanilineHCID 18429216HCID 18429216, compound

Product 1

HCID 18429174HCID 18429174, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

5-Amino-3-acetoxymethyl-N-(2,3-diacetoxypropyl)-2,4,6-triiodobenzamide (30.0 g, 40.3 mmol) was dissolved in dry N,N-dimethylacetamide (50 ml) and added dropwise to 2,3,4-triacetoxybutanoyl bromide (26.0 g, 0.93 mol) at 0° C. The mixture was stirred at ambient temperature for 5 h, and then added slowly to an aqueous solution of NaHCO3 (5%, 500 ml). A semi-crystalline precipitate was formed, filtered off and dissolved in ethyl acetate (200 ml). The organic phase was washed three times with diluted HCl (5%, 80 ml) and then twice with water (80 ml). After drying (Na2SO4) the solvent was evaporated to a semisolid residue. The residue was purified on a column of silica using methylene chloride/acetonitrile (4:1-3:2) as the eluent. The solvent was evaporated and the residue was further purified by preparative HPLC to give 13.8 g (35%) of the product.

Workup

  1. customA semi-crystalline precipitate was formed
  2. filtrationfiltered off
  3. dissolutiondissolved in ethyl acetate (200 ml)
  4. washThe organic phase was washed three times with diluted HCl (5%, 80 ml)
  5. dry with materialAfter drying (Na2SO4) the solvent
  6. customwas evaporated to a semisolid residue
  7. customThe residue was purified on a column of silica
  8. customThe solvent was evaporated
  9. customthe residue was further purified by preparative HPLC

Sources & evidence

ORD record
ord-69c360dd3d6e4e4e84d07c54dcde087f
Source dataset
uspto-grants-2002_09
Patent number
US06448442B1

Reaction notes

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