ChemicalBook CAS DataBase List Iopamidol

Iopamidol synthesis

6synthesis methods

Product Name:Iopamidol
CAS Number:60166-93-0
Molecular formula:C17H22I3N3O8
Molecular Weight:777.09

(S)-5-[2-(acetyloxy)propanamido]-2,4,6-triiodo-1,3-di(chloroformyl)benzene

60166-91-8
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534-03-2 Synthesis

534-03-2
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60166-93-0
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$59.00/25mg

Yield:60166-93-0 94%

Reaction Conditions:

in ISOPROPYLAMIDE at 8 - 20; for 10 h;

Steps:

8
680 g of S-(-)-5-((2-acetyloxy)-1-oxopropyl)amino)-2,4,6-triiodo-1,3-benzendicarboxylic acid dichloride (prepared as described in WO 96/37460) are dissolved in 1360 g of dimethylacetamide at room temperature and after cooling at 15°C [Solution A ]. 181 g of 2-ammino-1,3-propanediol purified with the method described in the previous Example 1 are dissolved in 1360 g of dimethylacetamide and added to the solution A in one hour at 8-15°C whilst stirring. The reaction is completed after ten hours at room temperature. The reaction mixture is concentrated at 100°C at 10 mbar until 98% of the solvent is distilled. 1700 g of water are added to the residue and the solution is purified using the method described in WO 97/30735.Yield on dry Iopamidol: 94% Contents of by-products determined with HPLC method (according to the method described in USP XXIII-NF, 1996, V°suppl.) = 0.11% The by-product N-[2-hydroxy-1-(hydroxymethyl)ethyl]-- N'-(2,3-dihydroxypropyl)-5-(2-hydroxy-1-oxopropyl)-2,4,6-triiodo-1,3-benzenedicarboxamide, coming from isoserinol, is under the detection limit. No presence of other by-products derived from 3-amino-1,2-propanediol are detected (see as ref. Pharmeuropa, 6, 343-345, 19949.

References:

BRACCO IMAGING S.p.A. EP883597, 2005, B1 Location in patent:Page/Page column 6-7

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618-88-2 Synthesis