October 2013
Intermediate to advanced
242 pages
9h 22m
English
Content preview from Methods of Non-a-Amino Acid Synthesis, 2nd Edition
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149Biologically Important Amino Acids
ammonium hydroxide followed by reaction with an acidic resin in water to convert
the alkenyl moiety to an alcohol gave GABOB.
170
A “heterocycle” strategy can also be used to prepare GABOB. A [3+2]-cycloaddi-
tion
171
reaction between 132 (prepared from glyoxylic acid)
172
and N-acetyl allylamine
generated dihydroisoxazole 133.
173
Treatment with methanolic potassium carbonate
gave lactam 134, and catalytic hydrogenation over Raney nickel opened the ring to
give the N-acetyl methyl ester of GABOB (135). Acid hydrolysis liberated GABOB.
173
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CO
2
H
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N
Cl
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O
N
O
N
AcHN
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2
Me
H
2
N
CO
2
H
Cl
NHAc
Cl
OMe
NHAc
HO
HO
NHAc
t-BuOCl
20 h
NCS
DMF ...
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