Water → HCID 18362189, compound

HRID 1280157Notes

Reaction equation

HRID 1280157 reaction equation
C([O:4][CH2:5][CH2:6][N:7]([C:17]1[C:18]([I:44])=[C:19]([CH2:39][O:40]C(=O)C)[C:20]([I:38])=[C:21]([C:36]=1[I:37])[C:22]([NH:24][CH2:25][CH:26]([O:32]C(=O)C)[CH2:27][O:28]C(=O)C)=[O:23])[C:8]([CH:10]1[CH2:14][O:13]C(C)(C)[O:11]1)=[O:9])(=O)C.[OH-].[Na+].O>CO>[OH:4][CH2:5][CH2:6][N:7]([C:8](=[O:9])[CH:10]([OH:11])[CH2:14][OH:13])[C:17]1[C:18]([I:44])=[C:19]([CH2:39][OH:40])[C:20]([I:38])=[C:21]([C:36]=1[I:37])[C:22]([NH:24][CH2:25][CH:26]([OH:32])[CH2:27][OH:28])=[O:23]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 18429243HCID 18429243, compound

Product 1

HCID 18362189HCID 18362189, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-[N′-(2-Acetoxyethyl)-2,2-dimethyl-1,3-dioxolane-4-carboxamido]-3-acetoxymethyl-N-(2,3-diacetoxypropyl)-2,4,6-triiodobenzamide (47 mg, 0.049 mmol) was dissolved in methanol (0.5 ml) and an aqueous solution of sodium hydroxide (2M, 0.25 ml) was added slowly followed by water (2 ml). After stirring at room temperature for 20 minutes, the reaction mixture was neutralized with a strongly acidic Son exchange resin. The resin was filtered off, and the filtrate acidified to pH=1 using hydrochloric acid (5M). After stirring at room temperature for 3.5 hours the reaction mixture was evaporated to dryness and the solid residue was purified by preparative HPLC giving 28 mg (76%) of product.

Workup

  1. filtrationThe resin was filtered off
  2. stirringAfter stirring at room temperature for 3.5 hours the reaction mixture
  3. customwas evaporated to dryness
  4. customthe solid residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-25a59117f41943f08e970f41e6598c5c
Source dataset
uspto-grants-2002_09
Patent number
US06448442B1

Reaction notes

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