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Title: Synthesis of N-formyl-3,4-di-t-butoxycarbonyloxy-6(trimethylstannyl)-L-phenylalanine ethyl ester and its regioselective radiofluorodestannylation to 6-[{sup 18}F]fluoro-L-dopa

Abstract

A protected 6-trimethylstannyl dopa derivative has been synthesized for the as a precursor for the preparation of 6-[{sup 18}F]fluoro-L-dopa. The tin derivative readily reacts with electrophilic radiofluorinating agents such as [{sup 18}F]F{sub 2}, [{sup 18}F]OF{sub 2} and [{sup 18}F]AcOF. The [{sup 18}F]fluoro intermediate was easily hydrolyzed with HBr and the product 6-[{sup 18}F]fluoro-L-dopa was isolated after HPLC purification in a maximum radiochemical yield of 23%, ready for human use. 1 fig.

Inventors:
; ; ;
Issue Date:
Research Org.:
University of California
OSTI Identifier:
27714
Patent Number(s):
5,393,908
Application Number:
PAN: 7-903,915; CNN: Grant PO1-NS-15654;Grant RO1-MH-37916
Assignee:
PTO; SCA: 550601; PA: EDB-95:059845; SN: 95001354447
DOE Contract Number:  
FC03-87ER60615
Resource Type:
Patent
Resource Relation:
Other Information: PBD: 28 Feb 1995
Country of Publication:
United States
Language:
English
Subject:
55 BIOLOGY AND MEDICINE, BASIC STUDIES; RADIOPHARMACEUTICALS; CHEMICAL PREPARATION; FLUORINE 18; LIQUID COLUMN CHROMATOGRAPHY; NUCLEAR MEDICINE

Citation Formats

Satyamurthy, N, Barrio, J R, Bishop, A J, and Namavari, M. Synthesis of N-formyl-3,4-di-t-butoxycarbonyloxy-6(trimethylstannyl)-L-phenylalanine ethyl ester and its regioselective radiofluorodestannylation to 6-[{sup 18}F]fluoro-L-dopa. United States: N. p., 1995. Web.
Satyamurthy, N, Barrio, J R, Bishop, A J, & Namavari, M. Synthesis of N-formyl-3,4-di-t-butoxycarbonyloxy-6(trimethylstannyl)-L-phenylalanine ethyl ester and its regioselective radiofluorodestannylation to 6-[{sup 18}F]fluoro-L-dopa. United States.
Satyamurthy, N, Barrio, J R, Bishop, A J, and Namavari, M. Tue . "Synthesis of N-formyl-3,4-di-t-butoxycarbonyloxy-6(trimethylstannyl)-L-phenylalanine ethyl ester and its regioselective radiofluorodestannylation to 6-[{sup 18}F]fluoro-L-dopa". United States.
@article{osti_27714,
title = {Synthesis of N-formyl-3,4-di-t-butoxycarbonyloxy-6(trimethylstannyl)-L-phenylalanine ethyl ester and its regioselective radiofluorodestannylation to 6-[{sup 18}F]fluoro-L-dopa},
author = {Satyamurthy, N and Barrio, J R and Bishop, A J and Namavari, M},
abstractNote = {A protected 6-trimethylstannyl dopa derivative has been synthesized for the as a precursor for the preparation of 6-[{sup 18}F]fluoro-L-dopa. The tin derivative readily reacts with electrophilic radiofluorinating agents such as [{sup 18}F]F{sub 2}, [{sup 18}F]OF{sub 2} and [{sup 18}F]AcOF. The [{sup 18}F]fluoro intermediate was easily hydrolyzed with HBr and the product 6-[{sup 18}F]fluoro-L-dopa was isolated after HPLC purification in a maximum radiochemical yield of 23%, ready for human use. 1 fig.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {1995},
month = {2}
}