High yield synthesis of 6-(/sup 18/F)fluoro-L-dopa by regioselective fluorination of protected L-dopa with (/sup 18/F)acetylhypofluorite

Journal Article · Mon Dec 01 04:00:00 EST 1986 · J. Nucl. Med.; (United States)

OSTI ID:6782214

Chaly, T; Diksic, M

Regioselective fluorination of a completely protected phosgene derivative of 3,4-dihydroxy-phenyl-L-alanine (5-(benzyl-3',4'-carbonate)-oxazolidine-2,5-dione) with gaseous /sup 18/F-labeled acetylhypofluorite and (/sup 18/F)F2 in acetonitrile is described. Fluorination with (/sup 18/F)acetylhypofluorite yields 6-(/sup 18/F)fluoro-L-dopa with 95% radiochemical purity; fluorination of the same substrate with (/sup 18/F)F2 yields a mixture of all three structural isomers in a ratio of 70:16:14 for 6-, 5-, and 2-fluoro compounds. Radiochemical yield, relative to (/sup 18/F) acetylhypofluorite, measured at the end of the synthesis, is (21 +/- 4)% (N = 8). The synthesis requires approximately 40 min (50 min if HPLC was done) and yields the final radiopharmaceutical in a two-step procedure. The specific activity of the final product was approximately 763 mCi/mmol at the end of a 40-min synthesis when 30-min irradiation was used.

• Research Organization: Montreal Neurological Institute and Hospital, Quebec
• OSTI ID: 6782214
• Journal Information: J. Nucl. Med.; (United States), Journal Name: J. Nucl. Med.; (United States) Vol. 12; ISSN JNMEA
• Country of Publication: United States
• Language: English

Related Subjects

38 RADIATION CHEMISTRY, RADIOCHEMISTRY, AND NUCLEAR CHEMISTRY
400702 -- Radiochemistry & Nuclear Chemistry-- Properties of Radioactive Materials
550601* -- Medicine-- Unsealed Radionuclides in Diagnostics
62 RADIOLOGY AND NUCLEAR MEDICINE
AMINO ACIDS
AUTONOMIC NERVOUS SYSTEM AGENTS
BETA DECAY RADIOISOTOPES
BETA-PLUS DECAY RADIOISOTOPES
CARBOXYLIC ACIDS
CHEMICAL PREPARATION
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
CHEMISTRY
DOPA
DRUGS
FLUORINATION
FLUORINE 18
FLUORINE ISOTOPES
HALOGENATION
HOURS LIVING RADIOISOTOPES
HYDROXY ACIDS
ISOTOPES
LABELLED COMPOUNDS
LABELLING
LIGHT NUCLEI
NEUROREGULATORS
NUCLEI
ODD-ODD NUCLEI
ORGANIC ACIDS
ORGANIC COMPOUNDS
RADIOCHEMISTRY
RADIOISOTOPES
RADIOPHARMACEUTICALS
SYNTHESIS
YIELDS