Pyridine → 3,5-Dioxohexanoic acid

HRID 1613030

Reaction equation

HRID 1613030 reaction equation
[OH:1][CH2:2][CH2:3]NCC(O)CO.C([O:13][C:14](=[O:16])[CH3:15])(=O)C.N1C=CC=CC=1.[CH3:23][C:24](N(C)C)=[O:25]>C(=O)([O-])[O-].[Na+].[Na+]>[CH3:23][C:24]([CH2:3][C:2]([CH2:15][C:14]([OH:13])=[O:16])=[O:1])=[O:25]

Participants

6

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 31374DimethylacetamideHCID 150349453-[(2-Hydroxyethyl)amino]propane-1,2-diol

Product 1

HCID 54598443,5-Dioxohexanoic acid

Reagents, catalysts & solvents 1

HCID 10340Sodium CarbonateSolvent

Procedure

As in Example 12, the title compound is prepared stepwise by first reacting 5-amino-2,4,6-triiodo-3-N-methylaminocarbonylbenzoyl chloride with 3-(N-2-hydroxyethyl)amino-1,2-propanediol dissolved in DMAc in the presence of sodium carbonate. The product, 5-amino-[N-(2,3-dihydroxypropyl)-N-(2-hydroxyethyl]-2,4,6-triiodo-3-N-methylaminocarbonylbenzamide, is reacted with acetic anhydride in the presence of pyridine to produce the triacetate, [N-(2-acetoxyethyl)-N-(2,3-diacetoxypropyl)]-5-amino-,4,6-triiodo-3-N-methylaminocarbonylbenzamide. This compound is then reacted with 2,4-dibromobutyryl bromide, prepared as in Example 12, Step B, and the product is then cyclized, hydrolyzed, and purified as in Example 12, Steps D and E to produce the final product.

Workup

  1. customAs in Example 12, the title compound is prepared stepwise

Sources & evidence

ORD record
ord-9c04cc339f34423f9076edeee02e5713
Source dataset
uspto-grants-1993_03
Patent number
US05191120

Linked notes

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