Sodium Iodide → 1,3-Dioxolan-2-one-4-yl 5-(N-acetylamino)-3-(N-acetyl-N-methylamino)-2,4,6-triiodobenzenecarboxylate

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Reaktionsgleichung

Cl[CH:2]1[CH2:6][O:5][C:4](=[O:7])[O:3]1.[C:8]([NH:11][C:12]1[C:13]([I:28])=[C:14]([N:23]([C:25](=[O:27])[CH3:26])[CH3:24])[C:15]([I:22])=[C:16]([C:19]([O-:21])=[O:20])[C:17]=1[I:18])(=[O:10])[CH3:9].[K+].[I-].[Na+]>CN(C=O)C>[C:8]([NH:11][C:12]1[C:13]([I:28])=[C:14]([N:23]([C:25](=[O:27])[CH3:26])[CH3:24])[C:15]([I:22])=[C:16]([C:19]([O:21][CH:2]2[CH2:6][O:5][C:4](=[O:7])[O:3]2)=[O:20])[C:17]=1[I:18])(=[O:10])[CH3:9]

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

4-Chloro-1,3-dioxolan-2-one (1.35 g, 11 mmol) was added at room temperature to a solution of potassium 5-(N-acetylamino)-3-(N-acetyl-N-methylamino)-2,4,6-triiodobenzenecarboxylate (6.66 g, 10 mmol) and sodium iodide (0.15 g, 1 mmol) in dry DMF (50 ml). After stirring at 50° C. for 6 hours and at room temperature for 4 days the solvent was removed at reduced pressure. The residue was dissolved in chloroform (100 ml) and washed four times with a saturated sodium hydrogen carbonate solution and finally twice with water. After treatment with magnesium sulfate the solution was finally evaporated to dryness. Yield: 5.6 g. Purity by HPLC: 93%. 1H-NMR (DMSO-d6): delta=1.67 (N (CH3)COCH3); 2.05(NCOCH3); 2.96(NCH3); 4.7; 4.9(CH2); 7.02(CH); 10.14 ppm(NH).

Aufarbeitung

customwas removed at reduced pressure
dissolutionThe residue was dissolved in chloroform (100 ml)
washwashed four times with a saturated sodium hydrogen carbonate solution
customAfter treatment with magnesium sulfate the solution was finally evaporated to dryness

Quellen und Nachweise

ORD-Eintrag: ord-3084609b75d9480abe7f172262f8b6da
Quelldatensatz: uspto-grants-1996_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05559266

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