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

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Reaction Conditions

Reaction Steps

1-Chloroethyl hexyl carbonate (0.47 g, 2.3 mmol) was added at room temperature to a solution of potassium 5-(N-acetylamino)-3-(N-acetyl-N-methylamino)-2,4,6-triiodobenzenecarboxylate (1.51 g, 2.3 mmol) and sodium iodide (0.036 g, 0.24 mmol) in dry DMF (12 ml). After stirring at 60° C. for 3 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 three 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: 0.88 g, Purity by HPLC: 95.2% 1H-NMR (DMSO-d6); delta=0.86 (CH2CH3); 1.22-1.36 (CH2CH2CH2CH3); 1.62 (OCH2CH2); 1.64 (CHCH3); 1.66 (NCH3COCH3); 2.04 (NHCOCH3); 2.95 (NCH3); 4.16 (OCH2); 6.96 (CH); 10.11 ppm (NH). FAB/MS: 801 ((M+H)+).

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