Sodium Bicarbonate → HCID 18429137, compound

HRID 1280176Notes

Reaction equation

HRID 1280176 reaction equation
[NH2:1][C:2]1[C:3]([I:40])=[C:4]([CH2:35][O:36][C:37](=[O:39])[CH3:38])[C:5]([I:34])=[C:6]([C:32]=1[I:33])[C:7]([N:9]([CH2:21][CH:22]([O:28]C(=O)C)[CH2:23][O:24]C(=O)C)[CH2:10][CH:11]([O:17]C(=O)C)[CH2:12][O:13]C(=O)C)=[O:8].[C:41]([O:44][CH:45]([CH2:49][CH2:50][CH2:51][Cl:52])[C:46](Cl)=[O:47])(=[O:43])[CH3:42].C(=O)([O-])O.[Na+]>CN(C)C(=O)C>[C:41]([O:44][CH:45]([CH2:49][CH2:50][CH2:51][Cl:52])[C:46]([NH:1][C:2]1[C:3]([I:40])=[C:4]([CH2:35][O:36][C:37](=[O:39])[CH3:38])[C:5]([I:34])=[C:6]([C:32]=1[I:33])[C:7]([N:9]([CH2:21][CH:22]([OH:28])[CH2:23][OH:24])[CH2:10][CH:11]([OH:17])[CH2:12][OH:13])=[O:8])=[O:47])(=[O:43])[CH3:42]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 18429191HCID 18429191, compoundHCID 18429279HCID 18429279, compound

Product 1

HCID 18429137HCID 18429137, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

5-Amino-3-acetoxymethyl-N,N-bis-(2,3-diacetoxypropyl)-2,4,6-triiodobenzamide, 6.85 mmol) was dissolved in dry N,N-dimethylacetamide (10 ml) and the mixture was cooled in an ice-bath. 2-Acetoxy-5-chloropentanoyl chloride (4.36 g, mmol) was then added dropwise. The mixture was stirred at room temperature for 24 h, and then added slowly to aqueous sodium hydrogen carbonate (5%, 600 ml) with efficient stirring. A precepitate was formed and filtered off, redissolved in methylene chloride (250 ml) which was washed with water (6×70 ml), dried Na2SO4) and concentrate in vacuo. The residue was chromatographed on a column of silica gel using heptane/ethyl acetate (3/7) as the eluent Yield: 7.30 g (97%).

Workup

  1. temperaturethe mixture was cooled in an ice-bath
  2. customA precepitate was formed
  3. filtrationfiltered off
  4. dissolutionredissolved in methylene chloride (250 ml) which
  5. washwas washed with water (6×70 ml), dried Na2SO4) and
  6. concentrationconcentrate in vacuo
  7. customThe residue was chromatographed on a column of silica gel

Sources & evidence

ORD record
ord-d992906332114d35a259cea78fe1ddfd
Source dataset
uspto-grants-2002_09
Patent number
US06448442B1

Reaction notes

Loading…