Sodium → N,N'-Bis[2,3-dihydroxypropyl)-5-(3-hydroxy-2-oxo-1-piperidinyl)-2,4,6-triiodo-1,3-benzenedicarboxamide

HRID 233072Notes

Reaction equation

HRID 233072 reaction equation
C([O:4][CH:5]1[CH2:10][CH2:9][CH2:8][N:7]([C:11]2[C:12]([I:47])=[C:13]([C:33]([NH:35][CH2:36][CH:37]([O:43]C(=O)C)[CH2:38][O:39]C(=O)C)=[O:34])[C:14]([I:32])=[C:15]([C:18]([NH:20][CH2:21][CH:22]([O:28]C(=O)C)[CH2:23][O:24]C(=O)C)=[O:19])[C:16]=2[I:17])[C:6]1=[O:48])(=O)C.C[O-].[Na+].[Na]>CO>[OH:43][CH:37]([CH2:38][OH:39])[CH2:36][NH:35][C:33]([C:13]1[C:12]([I:47])=[C:11]([N:7]2[CH2:8][CH2:9][CH2:10][CH:5]([OH:4])[C:6]2=[O:48])[C:16]([I:17])=[C:15]([C:18]([NH:20][CH2:21][CH:22]([OH:28])[CH2:23][OH:24])=[O:19])[C:14]=1[I:32])=[O:34]

Participants

5

Reactant 3

HCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 109531845-[3-(acetyloxy)-2-oxo-1-piperidinyl]-N,N'-bis[2,3-bis(acetyloxy)propyl]-2,4,6-triiodo-1,3-benzenedicarboxamide

Product 1

HCID 10440371N,N'-Bis[2,3-dihydroxypropyl)-5-(3-hydroxy-2-oxo-1-piperidinyl)-2,4,6-triiodo-1,3-benzenedicarboxamideYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

A solution of 5-[3-(acetyloxy)-2-oxo-1-piperidinyl]-N,N'-bis[2,3-bis(acetyloxy)propyl]-2,4,6-triiodo-1,3-benzenedicarboxamide of example 8c (4 g, 4.3 mmol) in methanol (20 ml) was treated with a solution of sodium methoxide in methanol, prepared from sodium (30 mg, 1.3 mmol) and anhydrous methanol (20 ml), and the mixture was stirred at room temperature for 2 hours. The pH of the solution was adjusted down to 7 by the addition of Dowex-50 (H+) resin. The mixture was filtered and the filtrate was freed of the solvent to obtain the crude product. Purification by low pressure reverse phase column chromatography over the CHP-20P resin furnished analytically pure N,N'-Bis[2,3-dihydroxypropyl)-5-(3-hydroxy-2-oxo-1-piperidinyl)-2,4,6-triiodo-1,3-benzenedicarboxamide as a snow-white glassy solid (2.3 g, 78% yield).

Workup

  1. additionThe pH of the solution was adjusted down to 7 by the addition of Dowex-50 (H+) resin
  2. filtrationThe mixture was filtered
  3. customto obtain the crude product
  4. customPurification by low pressure reverse phase column chromatography over the CHP-20P resin

Sources & evidence

ORD record
ord-4c3280d330724d8594d9f09caf43edd1
Source dataset
uspto-grants-1997_01
Patent number
US05591846

Reaction notes

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