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 977798Notes

Reaction equation

HRID 977798 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-5c66647e83c14d92bea5c29c7a64ecd6
Source dataset
uspto-grants-1997_03
Patent number
US05614638

Reaction notes

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