Water → HCID 18362189, compound

HRID 1604180Notes

Reaction equation

HRID 1604180 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 ion 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-ccc006343b5242b8be4c5ec53e6192fb
Source dataset
uspto-grants-1999_11
Patent number
US05993780

Reaction notes

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