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

HRID 36786

Reaktionsgleichung

[C:1](=[O:14])([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[O:2][CH:3](Cl)[CH3:4].[C:15]([NH:18][C:19]1[C:20]([I:35])=[C:21]([N:30]([C:32](=[O:34])[CH3:33])[CH3:31])[C:22]([I:29])=[C:23]([C:26]([O-:28])=[O:27])[C:24]=1[I:25])(=[O:17])[CH3:16].[K+].[I-].[Na+]>CN(C=O)C>[C:15]([NH:18][C:19]1[C:20]([I:35])=[C:21]([N:30]([C:32](=[O:34])[CH3:33])[CH3:31])[C:22]([I:29])=[C:23]([C:26]([O:28][CH:3]([O:2][C:1]([O:6][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:14])[CH3:4])=[O:27])[C:24]=1[I:25])(=[O:17])[CH3:16]

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

1-Chloroethyl benzyl carbonate (prepared according to Synthesis 1986, 627), (2.36 g, 11.0 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, 20 mmol) and sodium iodide (0.15 g, 1 mmol) in dry DMF (50 ml). After stirring at 50° C. for 7 hours and at room temperature for 7 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 twice with water. After treatment with magnesium sulfate the solution was evaporated to dryness. Yield: 6.8 g. Purity by HPLC: 97% 1H-NMR(DMSO-d6): delta=1.64 (CHCH3); 1.66(N(CH3)COCH3); 2.05 (NCOCH3); 5.23 (CH2); 7.00 (CH); 7.30-7.45(arom.); 10.12 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 evaporated to dryness

Quellen und Nachweise

ORD-Eintrag: ord-c713881e0cef418abec3afc1b461c234
Quelldatensatz: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05416223

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