Synthesis of 1-([18O2]-2-nitro-1-imidazolyl)-3-methoxy-2-propanol ([18O2]-misonidazole)

✍ Scribed by Chi-Ching Yang; Irving H. Goldberg

• Publisher: John Wiley and Sons
• Year: 1989
• Tongue: French
• Weight: 499 KB
• Volume: 27
• Category: Article
• ISSN: 0022-2135
• DOI: 10.1002/jlcr.2580270409

✦ Synopsis

A short, efficient synthesis for 1-(2-[180 2 ] -n i t r o -1 -i m i d a z o l y l ) -3methoxy-2-propanol ( [ I 8 0 2] -misonidazole) from 2-aminoimidazole is described. The required 180-labeled sodium nitrite (82.6 atom %) was conveiently synthesized by the treatment of sodium nitrite with DOWEX SOW ( H + ) in H2180. When 2-aminoimidazole reacted with excess of 180-labeled sodium nitrite in the presence of sulfuric acid containing copper sulfate in H2180, the 18O-labeled 2-nitroimidazole was formed with a reasonable yield (43%). [1802]-Misonidazole (70 atom %) was achieved with good yield by the coupling of sublimed 180-labeled 2-nitroimidazole with freshly distilled 1,2epoxy-3-methoxypropane in ethanol in the presence of a catalytic amount of anhydrous potassium carbonate under reflux for one hour. The desired product was purified by recrystalization and TLC, and characterized by 1H NMR and mass spectra. The 1 8 0 content and distribution of synthetic 1 8 0labeled misonidazole was determined from the FAB-MS spectra.