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Sharp R-120DW User Manual Page 85

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4 Tetram- und Tetronsäuren als β-Sekretase-Inhibitoren
61
DMF von der Schutzgruppe befreit. Die Bildung des so entstehenden freien Amins
konnte mittels Kaiser-Test kontrolliert werden.
[232]
HO
O
SH
TEA
CH
3
CN
HO
O
S R
R Br
Methode A:
oder
R
Cl
Methode B:
R
NH
2
Br
Br
O
N
H
O
Br R
HO
O
SH
TEA
CH
3
CN
HO
O
S
N
H
O
R
NaHCO
3
DCM
86-89
Schema 4.4. Methoden zur Synthese der Thioessigsäure-Derivate 30, 31, 35, 38-41 (Methode A) und
der Substanzen 33, 34, 36 und 37 (Methode B).
O
O
H
N
Fmoc
R
N
H
HO
O
S
R
R'
OH
O
S
R'
29-41
OH
22
N
H
OH
O
R
Fmoc
23-26
27
43-85
b
O
O
NH
2
R
28
c
O
O
H
N
R O
S
R'
d
42
a
Schema 4.5. Festphasenunterstüzte Synthese der Tetramsäuren 43-85. Reagenzien und
Bedingungen: (a) 2,6-Dichlorbenzoylchlorid, Pyridin, RT, 20 h, (b) 20% Piperidin in DMF, RT, 2 h, (c)
PyBOP, HOBt, DIEA, DMF, RT, 20 h, (d) KOBu
t
, THF, Rückfluss, 1 h.
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