Réaction #2275684

Équation de réaction

Acetic acid [(3,5-bis-chlorocarbonyl-2,4,6-triiodo-phenyl)-methyl-carbamoyl]-methyl ester

propanediol

DMA

methanol

→

acetic acid ({3-chlorocarbonyl-5-[(2,3-dihydroxy-propyl)-methyl-carbamoyl]-2,4,6-triiodo-phenyl}-methyl-carbamoyl)-methyl ester

Solvants

ethyl acetate

Conditions de réaction

Traitement

1. 1
   Lavagewashed with ice water/brine (50:50, 20 ml×3)
2. 2
   AutreThe organics were collected
3. 3
   Séchagedried over MgSO4
4. 4
   Filtrationfiltered
5. 5
   Autreevaporated to dryness
6. 6
   AutreThe product was purified by silica column chromatography
7. 7
   Lavageeluting with DCM

Mode opératoire

Acetic acid [(3,5-bis-chlorocarbonyl-2,4,6-triiodo-phenyl)-methyl-carbamoyl]-methyl ester (16.25 g, 22.9 mmol) and 3-methylamino-1,2,-propanediol (4.42 ml, 45.8 mmol) were stirred in DMA (80 ml) for 72 hours at room temperature. The mixture was diluted with ethyl acetate (150 ml) and washed with ice water/brine (50:50, 20 ml×3). The organics were collected, dried over MgSO4, filtered and evaporated to dryness. The product was purified by silica column chromatography eluting with DCM: methanol to give acetic acid ({3-chlorocarbonyl-5-[(2,3-dihydroxy-propyl)-methyl-carbamoyl]-2,4,6-triiodo-phenyl}-methyl-carbamoyl)-methyl ester (5.42 g, 6.96 mmol).

Source