S1
Concise solid-phase synthesis of inverse poly(amidoamine) dendrons using
AB
2
building blocks
Adela Ya-Ting Huang,
a
Ching-Hua Tsai,
a
Hsing-Yin Chen,
a
Hui-Ting Chen,
b
Chi-Yu Lu,
c
Yu-Ting Lin,
a
Chai-Lin Kao
a
*
a
Department of Medicinal and Applied Chemistry
b
Department of Fragrance and Cosmetic Science,
c
Department of Biochemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan
clkao@kmu.edu.tw
Synthesis and Characterization
To the solution of 3-bromopropylamine hydrobromide (2.0 g, 9.13 mmole) in CH
2
Cl
2
(30 mL) was added
triethylamine (4.1 g, 36.52 mmole, 4 eq) and stirred at rt for 30 min. To the resulting solution was added
di-tert-butyl-dicarbonate (2.42 g, 10.96 mmole, 1.2 eq) and stirred at rt under N
2
for 12 hours. The
resulting mixture was partitioned between ethyl acetate and H
2
O. The organic layer was washed with
brine and concentrated in vacuo to give an oily mixture which was further purified by column
chromatography (eluent: ethyl acetate: hexane=1:5) to give a colorless oil as product (2.13 g, 98 %, Rf =
0.5; eluent: ethyl acetate: hexane = 1:3).
1
H NMR (400 MHz,CDCl
3
) δ 1.43 (s, 9H), δ 2.04 (tt, J = 6.2,
6.4 Hz, 2H), δ 3.26 (br, 2H), δ 3.43 (t, J = 6.4 Hz, 2H), 4.67 (brs, 1H);
13
H NMR (400 MHz,CDCl
3
) δ
27.1, 28.2, 30.8, 32.9, 39.1, 156.1; HRMS (FAB) calcd for C
8
H
16
BrNO
2
[M
+
] 237.0364, found 237.0360.
0.5 0.5 1.0 1.0 1.5 1.5 2.0 2.0 2.5 2.5 3.0 3.0 3.5 3.5 4.0 4.0 4.5 4.5 5.0 5.0 5.5 5.5 6.0 6.0
Br NHBoc
5
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