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

HRID 36792

Reaktionsgleichung

Reaktionsgleichung von HRID 36792
[C:1](=[O:18])([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[O:2][CH:3](Cl)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:19]([NH:22][C:23]1[C:24]([I:39])=[C:25]([N:34]([C:36](=[O:38])[CH3:37])[CH3:35])[C:26]([I:33])=[C:27]([C:30]([O-:32])=[O:31])[C:28]=1[I:29])(=[O:21])[CH3:20].[K+].[I-].[Na+]>CN(C=O)C>[C:19]([NH:22][C:23]1[C:24]([I:39])=[C:25]([N:34]([C:36](=[O:38])[CH3:37])[CH3:35])[C:26]([I:33])=[C:27]([C:30]([O:32][CH:3]([O:2][C:1]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:18])[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[O:31])[C:28]=1[I:29])(=[O:21])[CH3:20]

Komponenten

5

Edukt 3

HCID 5238Sodium IodideHCID 23717801potassium 5-(N-acetylamino)3-(N-acetyl-N-methylamino)-2,4,6-triiodobenzenecarboxylateHCID 542165221-Chloro-1-phenylmethyl phenyl carbonate

Produkt 1

HCID 539927081-(Phenyloxycarbonyloxy)-1-phenylmethyl 5-(N-acetylamino)-3-(N-acetyl-N-methylamino)-2,4,6-triiodobenzenecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

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-triiodobenzene carboxylate (1.44 g, 2.2 mmol) and sodium iodide (0.034 g, 0.23 mmol) in dry DMF (12 ml). After stir ring 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+).

Aufarbeitung

  1. customat room temperature for 18 hours the solvent was removed at reduced pressure
  2. washwashed four times with a saturated sodium hydrogen carbonate solution
  3. dry with materialAfter drying with magnesium sulfate the solution
  4. customwas evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-47a7ada4de1a413cb36a1ac63104b27e
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05416223

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