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Methods of Non-a-Amino Acid Synthesis, 2nd Edition
book

Methods of Non-a-Amino Acid Synthesis, 2nd Edition

by Michael Bryant Smith
October 2013
Intermediate to advanced
242 pages
9h 22m
English
CRC Press
Content preview from Methods of Non-a-Amino Acid Synthesis, 2nd Edition
139Biologically Important Amino Acids
CO
2
Et
O
F
F
CO
2
Et
F F
CO
2
H
F F
NHBn NH
2
BnNH
2
, PhH
reux
cat. p-TsOH
1. NBH
3
CN
2N HCl/MeOH
2. 1N HCl
3. H
2
Pd-C
78 79 80
68%
30%
2-Pyrrolidinone derivatives are useful synthons for the preparation of 4-ami-
nobutanoic acid derivatives of all types. Ethyl pyroglutamate (81), derived from
L-glutamic acid, was converted to cyanomethyl-2-pyrrolidinone 82.
113
Reduction to
the amine and Cope elimination
114
gave 83, which was hydrolyzed to 4-aminohex-5-
enoic acid (84; known as vigabatrin). It is known that 84 is an irreversible inhibitor
of GABA-T. Due this mode of action, vigabatrin has been shown to increase levels
of GABA in t
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Publisher Resources

ISBN: 9781466577893