N,N'-bis-[2-acetyloxy-1-(acetyloxymethyl)ethyl]-5-[3-bromo-2-oxo-1-pyrrolidinyl]-2,4,6-triiodo-1,3-benzenedicarboxamide → N,N'-bis-[2-acetyloxy-1-(acetyloxymethyl)ethyl]-5-[3-acetyloxy-2-oxo-1-pyrrolidinyl]-2,4,6-triiodo-1,3-benzenedicarboxamide

HRID 1779857

Reaktionsgleichung

Reaktionsgleichung von HRID 1779857
[C:1]([O:4][CH2:5][CH:6]([NH:12][C:13]([C:15]1[C:20]([I:21])=[C:19]([N:22]2[CH2:26][CH2:25][CH:24](Br)[C:23]2=[O:28])[C:18]([I:29])=[C:17]([C:30]([NH:32][CH:33]([CH2:39][O:40][C:41](=[O:43])[CH3:42])[CH2:34][O:35][C:36](=[O:38])[CH3:37])=[O:31])[C:16]=1[I:44])=[O:14])[CH2:7][O:8][C:9](=[O:11])[CH3:10])(=[O:3])[CH3:2]>C(O)(=O)C.C([O-])(=O)C.[Ag+]>[C:1]([O:4][CH2:5][CH:6]([NH:12][C:13]([C:15]1[C:20]([I:21])=[C:19]([N:22]2[CH2:26][CH2:25][CH:24]([O:4][C:1](=[O:3])[CH3:2])[C:23]2=[O:28])[C:18]([I:29])=[C:17]([C:30]([NH:32][CH:33]([CH2:39][O:40][C:41](=[O:43])[CH3:42])[CH2:34][O:35][C:36](=[O:38])[CH3:37])=[O:31])[C:16]=1[I:44])=[O:14])[CH2:7][O:8][C:9](=[O:11])[CH3:10])(=[O:3])[CH3:2]

Komponenten

4

Edukt 1

HCID 19048411N,N'-bis-[2-acetyloxy-1-(acetyloxymethyl)ethyl]-5-[3-bromo-2-oxo-1-pyrrolidinyl]-2,4,6-triiodo-1,3-benzenedicarboxamide

Produkt 1

HCID 19048398N,N'-bis-[2-acetyloxy-1-(acetyloxymethyl)ethyl]-5-[3-acetyloxy-2-oxo-1-pyrrolidinyl]-2,4,6-triiodo-1,3-benzenedicarboxamideAusbeute 163,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11246Silver acetateKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

N,N'-bis-[2-acetyloxy-1-)acetyloxymethyl)ethyl]-5-[3-bromo-2-oxo-1-pyrrolidinyl]-2,4,6-triiodo-1,3-benzenedicarboxamide (4.00 g, 3.92 mmol) of example 4a was dissolved in glacial acetic acid (40 ml) and treated with silver acetate (3.25 g, 19.50 mmol) at 133°-135° for 26 hours under a nitrogen atmosphere. The suspended solids were filtered off and the solvent was removed in vacuo. The resulting crude residue was treated with acetic anhydride (30 ml) and pyridine (42 ml), after which the volatile components were completely removed under high vacuum. The resulting product was purified by silica gel flash chromatography to obtain N,N'-bis-[2-acetyloxy-1-(acetyloxymethyl)ethyl]-5-[3-acetyloxy-2-oxo-1-pyrrolidinyl]-2,4,6-triiodo-1,3-benzenedicarboxamide as a pale orange foam (3.20 g, 82% yield).

Aufarbeitung

  1. filtrationThe suspended solids were filtered off
  2. customthe solvent was removed in vacuo
  3. additionThe resulting crude residue was treated with acetic anhydride (30 ml) and pyridine (42 ml)
  4. customafter which the volatile components were completely removed under high vacuum
  5. customThe resulting product was purified by silica gel flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7ffbb2a337e14427acf6d22195fb3290
Quelldatensatz
uspto-grants-1997_05
Patentnummer
US05628980

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