Pleaseprovideamechanismforthefollowingtransformation

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Unformatted text preview: 
 
 
 
 
 
 
 Kawasaki
et
al.
JOC.
2001
(66).
1200­1204
 O CO2Me N Ph3P O N O MeO2C O N CO2Me 
 3.)
 a.
 The
following
artificial
amino
acid,
2,3‐diaminopropionic
acid
(DAP),
is
often
used
to
 probe
the
importance
of
side
chain
length
in
the
formation
of
protein
secondary
structure.

 Please
provide
a
mechanism
for
the
following
transformation.
 O O 
 1. , NEt3 H2N Cl O 
 HO O 
 Boc OMe Boc OMe 2. NaN3 N O N 
 3. Heat Boc Boc O Boc O 4. H2O 
 O 
 Cl O 
 O O O Cl O 
 O O HO NEt O O O 
 Boc O O OMe Boc OMe Boc OMe N N Boc OMe N N 
 Boc O Boc O Boc O Boc O 
 N N 
OO O O O MeOOCO N 
O O OCN NNN Boc OMe Boc OMe Boc OMe Boc OMe N N N Boc OMe 
 N N Boc O Boc O Boc O Boc O Boc O 
 OH 
 OH OH OH OCN O OCN HOH...
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This note was uploaded on 01/24/2014 for the course CHEM 436 taught by Professor White during the Spring '08 term at University of Illinois, Urbana Champaign.

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