title: [(11)C] Carbon monoxide in selenium-mediated synthesis of (11)C-carbamoyl compounds.
abstract: Using either amines, amino alcohols, or alcohols in selenium-mediated synthesis with [(11)C]carbon monoxide, 3 ureas, 6 carbamates, and 1 carbonate were labeled. Tetrabutylammonium fluoride ((TBA)F) was discovered to form a soluble and reactive complex with selenium and drastically increase the radiochemical yields. Of the selected carbamoyl compounds, one was a receptor ligand, one was an enzyme inhibitor, and one was a muscular relaxant pharmaceutical. The (11)C-target compounds were obtained in radiochemical yields ranging from low to almost quantitative and with specific radioactivity up to 1300 GBq/micromol. The radiochemical purity of the final products exceeded 98%. In one case, the corresponding (13)C-substituted compound was produced to verify the position of the (11)C-label. In a typical experiment starting with 16.4 GBq [(11)C]carbon monoxide, 7.0 GBq of LC-purified 5-phenyl-1,3-oxazolidin-[2-(11)C]-2-one was obtained within 20 min from start of the carbonylation reaction (84% decay-corrected radiochemical yield). The presented approach is an interesting alternative to the use of [(11)C]phosgene in labeling chemistry.
authors.affiliation: Department of Organic Chemistry, Institute of Chemistry, and Uppsala University PET Centre, Uppsala University, S-751 85 Uppsala, Sweden.
authors.forename: Tor
authors.initials: T
authors.lastname: Kihlberg
authors.forename: Farhad
authors.initials: F
authors.lastname: Karimi
authors.forename: Bengt
authors.initials: B
authors.lastname: Långström
mesh_terms: D002219:Carbamates / Q000138:chemical synthesis*; D002248:Carbon Monoxide / Q000737:chemistry*; D002250:Carbon Radioisotopes / Q000737:chemistry*; D002254:Carbonates / Q000138:chemical synthesis*; D007553:Isotope Labeling / Q000379:methods; D000644:Quaternary Ammonium Compounds / Q000737:chemistry; D019275:Radiopharmaceuticals / Q000138:chemical synthesis*; D012643:Selenium / Q000737:chemistry*; D014508:Urea / Q000031:analogs & derivatives* / Q000138:chemical synthesis
chemical_list: D002219:Carbamates; D002250:Carbon Radioisotopes; D002254:Carbonates; D000644:Quaternary Ammonium Compounds; D019275:Radiopharmaceuticals; D002248:Carbon Monoxide; D014508:Urea; C009405:tetrabutylammonium; D012643:Selenium