Sodium → HCID 10463137, compound

HRID 233076Notes

Reaction equation

HRID 233076 reaction equation
C([O:4][CH:5]([CH2:45][O:46]C(=O)C)[CH2:6][NH:7][C:8]([C:10]1[C:15]([I:16])=[C:14]([N:17]2[C:22](=[O:23])[CH2:21][O:20][CH2:19][CH:18]2[CH2:24][O:25]C(=O)C)[C:13]([I:29])=[C:12]([C:30]([NH:32][CH2:33][CH:34]([O:40]C(=O)C)[CH2:35][O:36]C(=O)C)=[O:31])[C:11]=1[I:44])=[O:9])(=O)C.C[O-].[Na+].[Na]>CO.O>[OH:40][CH:34]([CH2:35][OH:36])[CH2:33][NH:32][C:30]([C:12]1[C:13]([I:29])=[C:14]([N:17]2[C:22](=[O:23])[CH2:21][O:20][CH2:19][CH:18]2[CH2:24][OH:25])[C:15]([I:16])=[C:10]([C:8]([NH:7][CH2:6][CH:5]([OH:4])[CH2:45][OH:46])=[O:9])[C:11]=1[I:44])=[O:31]

Participants

6

Reactant 3

HCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 11766551HCID 11766551, compound

Product 1

HCID 10463137HCID 10463137, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

To a solution of N,N'-bis[2,3-bis(acetyloxy)propyl]-5-[3-(Acetyloxy)methyl-5-oxo-4-morpholinyl]-2,4,6-triiodo-1,3-benzenedicarboxamide (5.15 g, 5 mmol) in anhydrous methanol (100 ml), was added a solution of sodium methoxide, prepared from sodium (25 mg) and anhydrous methanol (5 ml), and the mixture was stirred for 3 hours. The solution was adjusted to pH 7 by a slow addition of Dowex-50 (H+) resin and then filtered. The filtrate was concentrated in vacuo to obtain the crude product (3.85 g) as a white solid. The material was dissolved in water (40 ml) and loaded onto a column of CHP-20 diaion resin. The column was first eluted with water (1 L) and then with a stepwise gradient of ethanol in water (1-8%). The fractions containing the pure product were combined and the solvents removed in vacuo to obtain N,N'-Bis(2,3-dihydroxypropyl)-5-[3-(hydroxymethyl)-5-oxo-4-morpholinyl]-2,4,6-triiodo-1,3-benzenedicarboxamide as a white microcrystalline solid (2.45 g, 60% yield, 99% purity). Recrystallization from ethanol/isopropanol (95/5) afforded the analytical sample as a white solid, m.p. 227°-230°.

Workup

  1. additionThe solution was adjusted to pH 7 by a slow addition of Dowex-50 (H+) resin
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo
  4. customto obtain the crude product (3.85 g) as a white solid
  5. washThe column was first eluted with water (1 L)
  6. additionThe fractions containing the pure product
  7. customthe solvents removed in vacuo

Sources & evidence

ORD record
ord-df313fc3929642de972ad8f52570bdd2
Source dataset
uspto-grants-1997_01
Patent number
US05591846

Reaction notes

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