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

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

Patent · Sat Dec 31 23:00:00 EST 1994

OSTI ID:869766

Satyamurthy, Nagichettiar ^[1]; Barrio, Jorge R ^[2]; Bishop, Allyson J ^[3]; Namavari, Mohammad ^[4]

1613 Barry Ave. - Apt. #9, Los Angeles, CA 90025
5920 Grey Rock Rd., Agoura Hills, CA 91301
1661 Selby Ave. - Apt. 5A, Los Angeles, CA 90024
3230 Overland Ave. - Apt. 121, Los Angeles, CA 90034

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.

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Research Organization:: University of California

DOE Contract Number:: FC03-87ER60615

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 Number(s):: US 5393908

OSTI ID:: 869766

Country of Publication:: United States

Language:: English

References (14)

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Fluorination of substituted veratroles via regioselective mercuration Luxen, A.; Barrio, J. R. Tetrahedron Letters, Vol. 29, Issue 13 https://doi.org/10.1016/S0040-4039(00)80335-4	journal	January 1988
Carbon-13 nuclear magnetic resonance studies of benzocycloalkenes and fluorobenzocycloalkenes Adcock, William; Gupta, B. D.; Khor, T. C. The Journal of Organic Chemistry, Vol. 41, Issue 5 https://doi.org/10.1021/jo00867a002	journal	March 1976
Fluorination of aromatic compounds with F2 and acetyl hypofluorite: synthesis of 18F-aryl fluorides by cleavage of aryl-tin bonds [1] Adam, M. J.; Ruth, T. J.; Jivan, S. Journal of Fluorine Chemistry, Vol. 25, Issue 3 https://doi.org/10.1016/S0022-1139(00)81207-5	journal	July 1984
Tin-119 chemical shifts of ortho, meta, para, 2,6-, and polysubstituted aryltrimethyltin derivatives and related organotin compounds Kroth, H. J.; Schumann, H.; Kuivila, H. G. Journal of the American Chemical Society, Vol. 97, Issue 7 https://doi.org/10.1021/ja00840a023	journal	April 1975
An approach to the asymmetric synthesis of l-6-[18F]fluorodopa via NCA nucleophilic fluorination Lemaire, Christian; Guillaume, Marcel; Cantineau, Robert International Journal of Radiation Applications and Instrumentation. Part A. Applied Radiation and Isotopes, Vol. 42, Issue 7 https://doi.org/10.1016/0883-2889(91)90033-W	journal	January 1991
Synthesis and purification of l-6-[18F]fluorodopa Adam, M. J.; Jivan, S. International Journal of Radiation Applications and Instrumentation. Part A. Applied Radiation and Isotopes, Vol. 39, Issue 12 https://doi.org/10.1016/0883-2889(88)90100-1	journal	January 1988
Reaction of [18F]acetyl hypofluorite with derivatives of dihydroxyphenylalanine: Synthesis of l-[18F]6-fluorodopa Adam, Michael J.; Grierson, John R.; Ruth, Thomas J. International Journal of Radiation Applications and Instrumentation. Part A. Applied Radiation and Isotopes, Vol. 37, Issue 8 https://doi.org/10.1016/0883-2889(86)90286-8	journal	January 1986
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-l-phenylalanine
-l-phenylalanine ethyl
/999/
18
23
4-di-t-butoxycarbonyloxy-6-
6-
6-trimethylstannyl
acof
agents
derivative
dopa
easily
electrophilic
ester
ethyl
ethyl ester
fluorinating agent
fluoro
fluoro-l-dopa
hbr
hplc
human
hydrolyzed
intermediate
isolated
maximum
n-formyl-3
precursor
preparation
product
protected
purification
radiochemical
radiofluorinating
radiofluorodestannylation
reacts
readily
regioselective
regioselective radiofluorodestannylation
synthesis
synthesized
trimethylstannyl
yield

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

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References (14)

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