Paper
Organic & Biomolecular Chemistry
low temperature (ice bath). After completion of the addition,
the viscous reaction mixture was left at room temperature for
References
3
h, and then 100 mL of ethanol were added. The precipitate
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formed was filtered off, and the filtrate was placed in an ice
bath for 1 h. The crystals of chlorohydrate 13 formed were
filtered off and dried under reduced pressure. The filtrate was
concentrated under vacuum, and cooled in an ice bath to
afford more product (9.3 g, 32%).
2
-Chloro-N,N-dimethylethanamine (13). To a solution of
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3.9), and the mixture was stirred for 10 min. The product was
extracted three times with diethyl ether (3 × 10 mL) and the
organic layer was dried with magnesium sulfate. After evapor-
1
1
ation, the product was obtained as a colorless oil. H-NMR
300 MHz, CDCl
3
(
6
3
, 300 K): δ (ppm) = 2.33 (s, 6H); 2.69 (t, J =
3
.7 Hz, 2H); 3.57 (t, J = 6.7 Hz, 2H).
-Azido-N,N-dimethylethanamine (10).
-chloro-N,N-dimethylethanamine 13 (500 mg, 4.65 mmol)
2
A
solution of
2
and sodium azide (670 mg, 10.31 mmol) in water (12.5 mL)
was stirred at 60 °C for 40 h. After cooling the reaction mixture
to room temperature, 0.5 g of potassium hydroxide was added
ice bath), and the product was extracted with diethyl ether
2 × 25 mL). The combined organic layers were dried over
magnesium sulfate and concentrated under vacuum. The
residue was dried under reduced pressure to afford
3
colorless oil (317 mg, 60%). H NMR (300 MHz, CDCl , 300 K):
(
(
a
1
3
3
δ (ppm) = 2.28 (s, 6H); 2.51 (t, J = 6.2 Hz, 2H); 3.35 (t, J = 6.2
Hz, 2H). C NMR (75 MHz, CDCl , 300 K): δ (ppm) = 45.6,
9.2, 58.2.
1
3
3
4
2547.
9
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Abbreviations
BBN
Bombesin
BBN–Chol Bombesin–cholesterol derivative
BCN
FPLC
HPLC
SubPc
DPPC
Trt
Bicyclononyne
Fast protein liquid chromatography
High performance liquid chromatography
Subphthalocyanine
1,2-Dipalmitoyl-sn-glycero-3-phosphocholine
Trityl
10 (a) P. Vabbilisetty and X.-L. Sun, Org. Biomol Chem., 2014,
12, 1237; (b) A. S. Gupta and H. A. von Recum, Bioconjuga-
tion Strategies: Lipids, Liposomes, Polymersomes, and
Microbubbles, in Chemistry of Bioconjugates: Synthesis,
Characterization, and Biomedical Applications, ed. R. Narain,
John Wiley & Sons, Inc., Hoboken, NJ, USA, 2014, p. 185;
Boc
Mmt
tert-Butoxycarbonyl
4,4′-Dimethoxytrityl
(
c) A. Accardo, G. Salsano, A. Morisco, M. Aurilio, A. Parisi,
Acknowledgements
F. Maione, C. Cicala, D. Tesauro, L. Aloj, G. De Rosa and
RAD and YB thank the Burgundy Regional Council, CRB
G. Morelli, Int. J. Nanomed., 2012, 7, 2007.
(
FABER Program), and RAD thanks CNRS for Chaire d’Excel- 11 S. Guard, K. J. Watling and W. Howson, Eur. J. Pharmacol.,
lence. This work was supported by the 3MIM agreement
1993, 240, 177.
(
CNRS, uB and CRB). MM thanks ANR (Equipex IMAPPI). We 12 V. Sancho Bornez, A. Di Florio, T. W. Moody and
also thank France Life Imaging (FLI).
R. T. Jensen, Curr. Drug Delivery, 2011, 8, 79.
Org. Biomol. Chem.
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