Potassium Carbonate → N,N'-bis[2,3-bis(acetyloxy)propyl]-5-(3-bromo-2-oxo-1-piperidinyl]-2,4,6-triiodo-1,3-benzenedicarboxamide

HRID 977803Notes

Reaction equation

HRID 977803 reaction equation
[C:1]([O:4][CH:5]([CH2:42][O:43][C:44](=[O:46])[CH3:45])[CH2:6][NH:7][C:8]([C:10]1[C:15]([I:16])=[C:14]([NH:17][C:18](=[O:25])[CH:19]([Br:24])[CH2:20][CH2:21][CH2:22]Br)[C:13]([I:26])=[C:12]([C:27]([NH:29][CH2:30][CH:31]([O:37][C:38](=[O:40])[CH3:39])[CH2:32][O:33][C:34](=[O:36])[CH3:35])=[O:28])[C:11]=1[I:41])=[O:9])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>CN(C)C(=O)C.C(OCC)(=O)C>[C:1]([O:4][CH:5]([CH2:42][O:43][C:44](=[O:46])[CH3:45])[CH2:6][NH:7][C:8]([C:10]1[C:15]([I:16])=[C:14]([N:17]2[CH2:22][CH2:21][CH2:20][CH:19]([Br:24])[C:18]2=[O:25])[C:13]([I:26])=[C:12]([C:27]([NH:29][CH2:30][CH:31]([O:37][C:38](=[O:40])[CH3:39])[CH2:32][O:33][C:34](=[O:36])[CH3:35])=[O:28])[C:11]=1[I:41])=[O:9])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 19048400N,N'-bis[2,3-bis(acetyloxy)propyl]-5-[(2,5-dibromo-1-oxopentyl)amino]-2,4,6-triiodo-1,3-benzenedicarboxamide

Product 1

HCID 19048418N,N'-bis[2,3-bis(acetyloxy)propyl]-5-(3-bromo-2-oxo-1-piperidinyl]-2,4,6-triiodo-1,3-benzenedicarboxamideYield 80%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution of N,N'-bis[2,3-bis(acetyloxy)propyl]-5-[(2,5-dibromo-1-oxopentyl)amino]-2,4,6-triiodo-1,3-benzenedicarboxamide of example 8a (20.7 g, 18.5 mmol) in N,N-dimethylacetamide (200 ml), was added powdered potassium carbonate (20 g, 92 mmol) and the mixture was stirred at room temperature for 5 hours. The resulting slurry was filtered and the filtrate freed of the solvent to obtain a light brown solid, which was redissolved in ethyl acetate (500 ml). The solution was washed with water (2×50 ml) and saturated aqueous sodium chloride (1×100 ml) and then dried over magnesium sulfate. The solvent was removed in vacuo and the crude product (18.1 g) purified by column chromatography over silica gel to obtain pure N,N'-bis[2,3-bis(acetyloxy)propyl]-5-(3-bromo-2-oxo-1-piperidinyl]-2,4,6-triiodo-1,3-benzenedicarboxamide as a white solid (14.04 g, 80% yield), m.p. 232°-35°.

Workup

  1. filtrationThe resulting slurry was filtered
  2. customto obtain a light brown solid, which
  3. washThe solution was washed with water (2×50 ml) and saturated aqueous sodium chloride (1×100 ml)
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed in vacuo
  6. customthe crude product (18.1 g) purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-d32dc2ab02d94d06941f7788f1fc54e7
Source dataset
uspto-grants-1997_03
Patent number
US05614638

Reaction notes

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