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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21Functional Group Exchanges
reaction
108,109
with Cbz-protected amino aldehyde 115. The product after hydrolysis was
conjugated acid 116.
110
Cleavage of the N-Cbz group with triuoroacetic acid gave
3-(1-cyclopropyl-1-amino)prop-2-enoic acid, 117.
CHO
NHCbz
CbzHN
H
2
N
CO
2
H
CO
2
H
1. (EtO)
2
POCH
2
CO
2
Et
NaH
2. KOH
3. H
3
O
+
TFA, HCl
115 116 117
50%
99%
A Wittig olenation
111
reaction was used to prepare an enamino-ester. The requisite
starting material (119) was prepared by reaction of n-butylmagnesium bromide and
isothiocyanate 118.
112
Ethyl N-thioacyl urethane 119 reacted with the Wittig reagent
shown to give 120.
113
This sequence was also used with methylmagnesium ...
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