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

Participants

Reaction Conditions

Reaction Steps

1-Chloro-1-phenylmethyl phenyl carbonate (0.63 g, 2.4 mmol) was added at room temperature to a solution of potassium 5-(N-acetylamino)-3-(N-acetyl-N-methylamino)-2,4,6-triiodobenzenecarboxylate (1.44 g, 2.2 mmol) and sodium iodide (0.034 g, 0.23 mmol) in dry DMF (12 ml). After stirring at 60° C. for 2 hours and at room temperature for 18 hours the solvent was removed at reduced pressure. The residue was suspended in chloroform (20 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: 0.90 g. Purity by HPLC: 96.6% 1H-NMR(DMSO-d6): delta=1.67 (NCH3COCH3); 2.05 (NHCOCH3); 2.96 (NCH3); 7.29-7.54 (phenyl); 7.71 (CH); 10.13 ppm (NH). FAB/MS: 854 (M+).

Provenance & Evidence