Sodium Iodide → Phenyloxycarbonyloxymethyl 5-(N-acetylamino)-3-(N-acetyl-N-methylamino)-2,4,6-triiodobenzenecarboxylate

Participants

Reaction Conditions

Reaction Steps

Chloromethyl phenyl carbonate (0.50 g, 2.7 mmol) was added at room temperature to a solution of potassium 5-(N-acetylamino)-3-(N-acetyl-N-methylamino)-2,4,6-triiodobenzenecarboxylate (1.62 g, 2.4 mmol) and sodium iodide (0.038 g, 0.25 mmol) in dry DMF (15 ml). After stirring at 50° C. for 5 hours and at room temperature for 18 hours the solvent was removed at reduced pressure. The residue was suspended in chloroform (25 ml) and washed four times with a saturated sodium hydrogen carbonate solution and finally twice with water. After drying with magnesium sulfate the solution was evaporated to dryness. Yield: 0.67 g Purity by HPLC: 99.2% 1H-NMR(DMSO-d6): delta=1.68 (NCH3COCH3); 2.06 (NHCOCH3); 2.97 (NCH3); 6.08 (CH2); 7.28-7.49 (phenyl); 10.14 ppm (NH) . FAB/MS: 779 ((M+H)+).

Provenance & Evidence