Sodium Iodide → 1-(Phenyloxycarbonyloxy)pentyl 5-(N-acetylamino)-3-(N-acetyl-N-methylamino)-2,4,6-triiodobenzenecarboxylate

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Reaction Conditions

Reaction Steps

1-Chloropentyl phenyl carbonate (0.14 g, 0.58 mmol) was added at room temperature to a solution of potassium 5-(N-acetylamino)-3-(N-acetyl-N-methylamino)-2,4,6-triiodobenzenecarboxylate (0.35 g, 0.53 mmol) and sodium iodide (0,008 g, 0.053 mmol) in dry DMF (3 ml). After stirring at 50° C. for 5 hours and at room temperature for 2 days the solvent was removed at reduced pressure. The residue was suspended in chloroform (15 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: 0.04 g. Purity by HPLC: 94.8% 1H-NMR (DMSO-d6): delta=0.92(CH3CH2); 1.31-1.55 (CH3CH2CH2); 1.68 (NCH3COCH3); 2.04 (CH2CH); 2.05 (NHCOCH3); 2.97 (NCH3); 6.95 (CH); 7.27-7.49 (phenyl); 10.13 ppm (NH). FAB/MS: 835 ((M+H)+).

Provenance & Evidence