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

HRID 977807Notes

Reaction equation

HRID 977807 reaction equation
[C:1]([O:4][CH2:5][CH:6]([NH:12][C:13]([C:15]1[C:20]([I:21])=[C:19]([NH:22][C:23](=[O:30])[CH:24]([Br:29])[CH2:25][CH2:26][CH2:27]Br)[C:18]([I:31])=[C:17]([C:32]([NH:34][CH:35]([CH2:41][O:42][C:43](=[O:45])[CH3:44])[CH2:36][O:37][C:38](=[O:40])[CH3:39])=[O:33])[C:16]=1[I:46])=[O:14])[CH2:7][O:8][C:9](=[O:11])[CH3:10])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>CC(N(C)C)=O>[C:9]([O:8][CH2:7][CH:6]([NH:12][C:13]([C:15]1[C:20]([I:21])=[C:19]([N:22]2[CH2:27][CH2:26][CH2:25][CH:24]([Br:29])[C:23]2=[O:30])[C:18]([I:31])=[C:17]([C:32]([NH:34][CH:35]([CH2:41][O:42][C:43](=[O:45])[CH3:44])[CH2:36][O:37][C:38](=[O:40])[CH3:39])=[O:33])[C:16]=1[I:46])=[O:14])[CH2:5][O:4][C:1](=[O:3])[CH3:2])(=[O:11])[CH3:10]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 19048392N,N'-bis[2-(acetyloxy)-1-[(acetyloxy)methyl)ethyl]-5-[(2,5-dibromo-1-oxopentyl)amino]-2,4,6-triiodo-1,3-benzenedicarboxamide

Product 1

HCID 19048391N,N'-Bis[2-(acetyloxy)-1-[(acetyloxy)methyl]ethyl]-5-(3-bromo-2-oxo-1-piperidinyl)-2,4,6-triiodo-1,3-benzenedicarboxamideYield 98%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of N,N'-bis[2-(acetyloxy)-1-[(acetyloxy)methyl]ethyl]-5-[(2,5-dibromo-1-oxopentyl)amino]-2,4,6-triiodo-1,3-benzenedicarboxamide of example 9a (32.5 g, 29.1 mmol) in dimethylacetamide (250 ml), was added powdered potassium carbonate (25.2 g, 116.5 mmol). After stirring for 4 hours, the mixture was filtered. The filtrate was freed of the solvent in vacuo at 45° C. and the resulting solid was redissolved in ethyl acetate (500 ml). The ethyl acetate solution was washed with water (2×50 ml) and saturated aqueous sodium chloride (1×100 ml), and dried over anhydrous magnesium sulfate. The solvent was removed in vacuo to obtain a white solid (29.5 g) which, upon crystallization from ethyl acetate (1.2 L), furnished analytically pure N,N'-bis[2-acetyloxy)-1-[(acetyloxy) -methyl]ethyl]-5-(3-bromo-2-oxo-1-piperidinyl)-2,4,6-triiodo-1,3-benzenedicarboxamide as a white crystalline solid (23.95 g, 79.5% yield), m.p. 231°-3°.

Workup

  1. filtrationthe mixture was filtered
  2. customwas freed of the solvent in vacuo at 45° C.
  3. dissolutionthe resulting solid was redissolved in ethyl acetate (500 ml)
  4. washThe ethyl acetate solution was washed with water (2×50 ml) and saturated aqueous sodium chloride (1×100 ml)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-3ec43f2ea8c14a72a6f0d6eca2857852
Source dataset
uspto-grants-1997_03
Patent number
US05614638

Reaction notes

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