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O
O
O
H
N
NaHCO
3
(1.5 equiv)
xHCl·
H
2
N
BocHN
+
CO
2
+
NaCl
BocN
O
OMe
OMe
Ball-mill, 2 h, 3800 rpm
R
2
R
2
R
1
R
1
O
O
b
-UNCAs
a
-aminoesters
a
,
b
-dipeptidesv
O
O
O
O
N
N
N
N
BocHN
BocHN
BocHN
BocHN
OMe
OMe
OMe
OMe
O
O
O
O
Ph
Boc-
b
-Ala-Gly-OMe
88%
Boc-
b
-Ala-Ala-OMe
88%
Boc-
b
-Ala-Leu-OMe
87%
Boc-
b
-Ala-Phe-OMe
83%
O
O
O
O
N
N
H
N
N
BocHN
BocHN
BocHN
BocHN
OMe
OMe
OMe
OMe
O
O
O
O
MeO
O
NH
N
-Ala-His-OMe
a
91%
Boc-(
S
)-
b
3
-Chg(OMe)-Ala-OMe
79%
Boc-
b
-Ala-Val-OMe
82%
Boc-
b
-Ala-Ile-OMe
80%
Boc-
b
a
2 equiv of NaHCO
3
were used.
Scheme 6.17 Mechanosynthesis of a,b-dipeptides from b-UNCAs and a-aminoesters.
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