1,4,7,10-Tetraazacyclododecane → N-(3-carboxy-2,4,6-triiodophenyl)-1,4,7,10-tetraazacyclododecane-1-acetamide

HRID 2258393Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2258393
[NH:1]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8][NH:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[CH2:14][C:15]([NH:17][C:18]1[C:19]([I:29])=[C:20]([C:24]([I:28])=[CH:25][C:26]=1[I:27])[C:21]([OH:23])=[O:22])=[O:16]>CC#N>[C:21]([C:20]1[C:19]([I:29])=[C:18]([NH:17][C:15](=[O:16])[CH2:14][N:1]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8][NH:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]2)[C:26]([I:27])=[CH:25][C:24]=1[I:28])([OH:23])=[O:22]

Komponenten

4

Edukt 2

HCID 649631,4,7,10-TetraazacyclododecaneHCID 229213943-[(2-Chloroacetyl)amino]-2,4,6-triiodobenzoic acid

Produkt 1

HCID 22921403N-(3-carboxy-2,4,6-triiodophenyl)-1,4,7,10-tetraazacyclododecane-1-acetamideAusbeute 90,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

To a solution of 143.9 g of 1,4,7,10-tetraazacyclododecane (product commercially available) (0.84 mol) in 1000 ml of CH3CN under reflux, a suspension of 50 g of compound (A) 3-[(2-chloro-1-oxoethyl)amino]-2,4,6-triiodobenzoic acid (0.084 mol) in 500 ml of CH3CN is added during 1 h. The mixture is kept under reflux for 24 h, yielding a solid precipitation. The reaction mixture is filtered and the solid is purified by chromatography on silica gel. 55 g of N-(3-carboxy-2,4,6-triiodophenyl)-1,4,7,10-tetraazacyclododecane-1-acetamide (0.076 mol) are obtained.

Aufarbeitung

  1. additionis added during 1 h
  2. temperatureunder reflux for 24 h
  3. customyielding
  4. customa solid precipitation
  5. filtrationThe reaction mixture is filtered
  6. customthe solid is purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-4c6e37d1fb6a420b97990a4d55aa35cb
Quelldatensatz
uspto-grants-1997_08
Patentnummer
US05660814

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