N,N'-Bis-[2,3-diacetyloxypropyl]-5-[3-bromo-2-oxo-1-pyrrolidinyl]2,4,6-triiodo-1,3-benzenedicarboxamide → N,N'-bis-[2,3-diacetyloxypropyl]-5-[3-acetyloxy-2-oxo-1-pyrrolidinyl]-2,4,6-triiodo-1,3-benzenedicarboxamide

HRID 233064Notes

Reaction equation

HRID 233064 reaction equation
[C:1]([O:4][CH:5]([CH2:40][O:41][C:42](=[O:44])[CH3:43])[CH2:6][NH:7][C:8]([C:10]1[C:15]([I:16])=[C:14]([N:17]2[CH2:21][CH2:20][CH:19](Br)[C:18]2=[O:23])[C:13]([I:24])=[C:12]([C:25]([NH:27][CH2:28][CH:29]([O:35][C:36](=[O:38])[CH3:37])[CH2:30][O:31][C:32](=[O:34])[CH3:33])=[O:26])[C:11]=1[I:39])=[O:9])(=[O:3])[CH3:2]>C(O)(=O)C.C([O-])(=O)C.[Ag+]>[C:1]([O:4][CH:5]([CH2:40][O:41][C:42](=[O:44])[CH3:43])[CH2:6][NH:7][C:8]([C:10]1[C:15]([I:16])=[C:14]([N:17]2[CH2:21][CH2:20][CH:19]([O:4][C:1](=[O:3])[CH3:2])[C:18]2=[O:23])[C:13]([I:24])=[C:12]([C:25]([NH:27][CH2:28][CH:29]([O:35][C:36](=[O:38])[CH3:37])[CH2:30][O:31][C:32](=[O:34])[CH3:33])=[O:26])[C:11]=1[I:39])=[O:9])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 19048424N,N'-Bis-[2,3-diacetyloxypropyl]-5-[3-bromo-2-oxo-1-pyrrolidinyl]2,4,6-triiodo-1,3-benzenedicarboxamide

Product 1

HCID 19048410N,N'-bis-[2,3-diacetyloxypropyl]-5-[3-acetyloxy-2-oxo-1-pyrrolidinyl]-2,4,6-triiodo-1,3-benzenedicarboxamideYield 141.4%

Reagents, catalysts & solvents 2

HCID 11246Silver acetateCatalystHCID 176Acetic AcidSolvent

Procedure

N,N'-Bis-[2,3-diacetyloxypropyl]-5-[3-bromo-2-oxo-1-pyrrolidinyl]-2,4,6-triiodo-1,3-benzenedicarboxamide of example 5a, (6.43 g, 6.30 mmol) was dissolved in glacial acetic acid (63 ml) and then treated with silver acetate (4.21 g, 25.21 mmol) at reflux under nitrogen for 26 hours. The reaction mixture was cooled to room temperature and the solids filtered off. The solvent was evaporated in vacuo and the residue was partitioned between ethyl acetate and brine. The organic layer was dried and removal of the solvent afforded the crude product as a colored foam. Purification by silica gel flash chromatography furnished N,N'-bis-[2,3-diacetyloxypropyl]-5-[3-acetyloxy-2-oxo-1-pyrrolidinyl]-2,4,6-triiodo-1,3-benzenedicarboxamide as an off-white foam (4.45 g, 71% yield).

Workup

  1. temperatureat reflux under nitrogen for 26 hours
  2. filtrationthe solids filtered off
  3. customThe solvent was evaporated in vacuo
  4. customthe residue was partitioned between ethyl acetate and brine
  5. customThe organic layer was dried
  6. customremoval of the solvent
  7. customafforded the crude product as a colored foam
  8. customPurification by silica gel flash chromatography

Sources & evidence

ORD record
ord-516ee999b8694fddb9217ea71209bb14
Source dataset
uspto-grants-1997_01
Patent number
US05591846

Reaction notes

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