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AcOEt, 2:1) to give compound 8 as a white solid (0.12 m,
84%). 1H NMR (300 MHz, CDCl3): d 10.04 (s, 1H), 8.36 (d,
J ¼ 8.9 Hz, 1H), 8.22 (d, J ¼ 8.9 Hz, 1H), 7.63–7.46 (m,
2H), 7.41 (s, 1H), 5.51 (s, 1H), 3.40–3.16 (m, 4H), 2.31 (d,
J ¼ 7.1 Hz, 4H), 1.87 (dt, J1 ¼ 13.1 Hz, J2 ¼ 6.6 Hz, 2H),
1.54 (d, J ¼ 6.8 Hz, 2H), 1.25 (s, 10H), 0.99 (d, J ¼ 6.5 Hz,
12H), 0.86 (d, J ¼ 6.8 Hz, 3H). 13C NMR (126 MHz,
CDCl3): d 171.1, 155.5, 137.4, 135.0, 129.2, 128.3, 128.0,
127.3, 120.5, 119.2, 117.1, 115.3, 64.6, 61.4, 40.5, 31.9,
30.2, 29.4, 29.3, 27.1, 26.5, 22.7, 21.2, 14.2. MS (ESI): m/z
551.5 [M þ H]þ. HR-MS (ESI): calcd for C29H45N4O2Cl2
[M þ H]þ: 551.2914. Found: 551.2921.
Compound 9
To a mixture of compound 12 (0.50 g, 3.20 mmol) and
n-octanoic acid (1.3 mL, 8.23 mmol) in dichloromethane
(20 mL) were added N-hydroxybenzotrizole (0.85 mg,
6.30 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbo-
diimide hydrochloride (1.89 g, 9.80 mmol). The solution
was stirred for 24 h and then dichloromethane (20 mL) was
added. The solution was washed with diluted hydrochloric
acid (1 N, 20 mL), saturated sodium bicarbonate solution
(20 mL), water (20 mL £ 2) and brine (20 mL) and dried
over sodium sulfate. After the solvent was removed under
reduced pressure, the resulting residue was subjected to
column chromatography (petroleum ether:AcOEt, 3:1) to
afford compound 9 as a white solid (0.91 g, 70%). 1H NMR
(400 MHz, CDCl3): d 8.03 (s, 2H), 7.72 (d, J ¼ 8.7 Hz, 2H),
7.47 (d, J ¼ 8.5 Hz, 2H), 7.27 (s, 2H), 2.41 (t, J ¼ 7.6 Hz,
4H), 1.84–1.69 (m, 4H), 1.31 (t, J ¼ 22.6 Hz, 16H), 0.89 (t,
J ¼ 6.8 Hz, 6H). 13C NMR (101 MHz, CDCl3): d 171.8,
136.4, 134.5, 128.5, 126.5, 119.1, 116.1, 46.0, 38.0, 31.8,
29.3, 25.81, 22.8, 14.2. MS (MALDI-FT): m/z 411.3
[M þ H]þ. HR-MS (MALDI-FT): calcd for C26H39N2O2
[M þ H]þ: 411.3006. Found: 411.3013.
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Disclosure statement
No potential conflict of interest was reported by the authors.
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J. Org. Chem. 2001, 863–873; (b) Rahman, A.N.M.M.;
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2003, 72–81; (c) Desiraju, G.R. Chem. Commun. 2005,
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Funding
This work was supported by the National Natural Science
Foundation[grant numbers91227108and21228203]andMinistry
of Science and Technology [grant number 2013CB834501] of
China, and Science and Technology Commission of Shanghai
Municipality [grant number 13NM1400200].
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Supplemental data
Supplemental data for this article can be accessed here: http://dx.
(12) (a) Raja, R.; Thomas, J.M.; Jones, M.D.; Johnson, B.F.G.;
Vaughan, D.E.W. J. Am. Chem. Soc. 2003, 125, 14982–
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