2-[[2-[3-(Acetylamino)-2,4,6-triiodophenoxy]ethoxy]methyl]butanoic acid

Iopronic acid is an aromatic amide.

,A solution of 192 g 3-acetylamino-2,4,6-triiodophenol, sodium (0.35 mol) in 350 ml dimethylacetamide, was mixed with 107.5 g 3-(2-iodoethoxy)-2- ethylpropionic acid ethyl ester (0.35 mol) at 90°C with stirring over a period of about 20 to 30 minutes. Stirring was continued while the mixture was held at 95°C to 100°C for 16 hours. The solvent was then removed by distillation in a vacuum, and the residue was poured into 4,000 ml water. The solid precipitate formed was recovered and washed with water, dilute sodium carbonate solution, dilute sodium bisulfite solution, and again with much water. The ethyl ester was obtained in a yield of 220 g (90%). When recrystallized from 75% aqueous ethanol, it melted at 80°C to 86°C. The ester (70 g, 0.1 mol) was saponified in a boiling mixture of 250 ml methanol and 250 ml water to which 100 ml N sodium hydroxide solution was added in small batches with stirring. The methanol was distilled from the saponification mixture, the residue was mixed with water and extracted with ethyl acetate. The aqueous phase was acidified with hydrochloric acid in the presence of sodium bisulfite. The free acid gradually crystallized from the acidified solution in the amount of42.4 g (63% yield). When recrystallized from 50% ethanol and from ethyl acetate, it melted at 130°C.

Diagnostic aid (radiopaque medium, cholecystographic).

Molecular Weight:673.02
XLogP3:3.3
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:9
Exact Mass:672.8319
Monoisotopic Mass:672.8319
Topological Polar Surface Area:84.9
Heavy Atom Count:24
Complexity:426
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes