Water → Iopamidol

HRID 1797448Notes

Reaction equation

HRID 1797448 reaction equation
C([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])[C@@H:24]([O:26]C(=O)C)[CH3:25])[C:18]([I:31])=[C:17]([C:32]([NH:34][CH:35]([CH2:41][O:42]C(=O)C)[CH2:36][O:37]C(=O)C)=[O:33])[C:16]=1[I:46])=[O:14])[CH2:7][O:8]C(=O)C)(=O)C.O.[OH-].[Na+]>CO>[OH:42][CH2:41][CH:35]([NH:34][C:32]([C:17]1[C:18]([I:31])=[C:19]([NH:22][C:23](=[O:30])[C@@H:24]([OH:26])[CH3:25])[C:20]([I:21])=[C:15]([C:13]([NH:12][CH:6]([CH2:7][OH:8])[CH2:5][OH:4])=[O:14])[C:16]=1[I:46])=[O:33])[CH2:36][OH:37]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 11263180Penta-O-acetyliopamidol

Product 1

HCID 65492Iopamidol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

(S)-N,N′-Bis[2-acetyloxy-1-[(acetyloxy)methyl]ethyl]-5-[(2-acetyloxy-1-oxopropyl)amino]-2,4,6-triiodo-1,3-benzenedicarboxamide (4.9 g, 5 mmol) prepared in Example 4 is admixed with deionized water (30 mL) and methanol (30 mL). The suspension is warmed to 50° C., then 2 M NaOH (12.8 mL) is dripped therein over a period of 4 hours, keeping the pH of the mixture in the range of from 0 to 11. The solution is purified on ion exchange resins columns and the neutral eluate thus obtained is concentrated under vacuum and the residue is crystallized from ethanol to give the compound of the title (2.8 g, 3.6 mmol)

Workup

  1. customThe solution is purified on ion exchange resins columns
  2. customthe neutral eluate thus obtained
  3. concentrationis concentrated under vacuum
  4. customthe residue is crystallized from ethanol
  5. customto give the compound of the title (2.8 g, 3.6 mmol)

Sources & evidence

ORD record
ord-50ff4b6f22394fef9b9bc88e02d53db9
Source dataset
uspto-grants-2006_04
Patent number
US07034183B2

Reaction notes

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