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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.

Inventors:
 [1];  [2];  [3];  [4]
  1. 1613 Barry Ave. - Apt. #9, Los Angeles, CA 90025
  2. 5920 Grey Rock Rd., Agoura Hills, CA 91301
  3. 1661 Selby Ave. - Apt. 5A, Los Angeles, CA 90024
  4. 3230 Overland Ave. - Apt. 121, Los Angeles, CA 90034
Issue Date:
Research Org.:
Univ. of California (United States)
OSTI Identifier:
869766
Patent Number(s):
5393908
Assignee:
Satyamurthy, Nagichettiar (1613 Barry Ave. - Apt. #9, Los Angeles, CA 90025);Barrio, Jorge R. (5920 Grey Rock Rd., Agoura Hills, CA 91301);Bishop, Allyson J. (1661 Selby Ave. - Apt. 5A, Los Angeles, CA 90024);Namavari, Mohammad (3230 Overland Ave. - Apt. 121, Los Angeles, CA 90034)
Patent Classifications (CPCs):
C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07F - ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07C - ACYCLIC OR CARBOCYCLIC COMPOUNDS
DOE Contract Number:  
FC03-87ER60615
Resource Type:
Patent
Country of Publication:
United States
Language:
English
Subject:
synthesis; n-formyl-3; 4-di-t-butoxycarbonyloxy-6-; trimethylstannyl; -l-phenylalanine; ethyl; ester; regioselective; radiofluorodestannylation; 6-; 18; fluoro-l-dopa; protected; 6-trimethylstannyl; dopa; derivative; synthesized; precursor; preparation; readily; reacts; electrophilic; radiofluorinating; agents; acof; fluoro; intermediate; easily; hydrolyzed; hbr; product; isolated; hplc; purification; maximum; radiochemical; yield; 23; human; regioselective radiofluorodestannylation; fluorinating agent; ethyl ester; -l-phenylalanine ethyl; /999/

Citation Formats

Satyamurthy, Nagichettiar, Barrio, Jorge R, Bishop, Allyson J, and Namavari, Mohammad. 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, Nagichettiar, Barrio, Jorge R, Bishop, Allyson J, & Namavari, Mohammad. 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, Nagichettiar, Barrio, Jorge R, Bishop, Allyson J, and Namavari, Mohammad. Sun . "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. https://www.osti.gov/servlets/purl/869766.
@article{osti_869766,
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, Nagichettiar and Barrio, Jorge R and Bishop, Allyson J and Namavari, Mohammad},
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.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {1995},
month = {1}
}

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