J
I. I. Jevtić et al.
Paper
Synthesis
Methyl 2-Ethoxyphenylcarbamate (2u)
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Prepared according to the general procedure for NBA from 2-ethoxy-
benzamide (1t; 0.20 g, 1.2 mmol) in MeOH (3 mL), LiOH·H2O (0.10 g,
2.4 mmol) and NBA (0.16 g, 1.2 mmol), over 24 h. The crude product
was dissolved in hexane, the impurities were removed by filtration
and the filtrate was concentrated.
Yield: 0.20 g (85%); colorless oil.
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Davis, J. A.; Dudley, D. A.; Edmunds, J. J.; Esmaeil, N.; Geyer, A.;
Heemstra, R. J.; Jalaie, M.; Ohren, J. F.; Ostroski, R.; Ellis, T.;
Schaum, R. P.; Stoner, C. J. Med. Chem. 2011, 54, 4219.
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A.; Jeong, B.-S. Org. Biomol. Chem. 2014, 12, 8702.
(23) Mirguet, O.; Lamotte, Y.; Donche, F.; Toum, J.; Gellibert, F.;
Bouillot, A.; Gosmini, R.; Nguyen, V.-L.; Delannée, D.; Seal, J.;
Blandel, F.; Boullay, A.-B.; Boursier, E.; Martin, S.; Brusq, J.-M.;
Krysa, G.; Riou, A.; Tellier, R.; Costaz, A.; Huet, P.; Dudit, Y.;
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1H NMR (200 MHz, CDCl3): δ = 8.08 (br s, 1 H), 7.26 (br s, 1 H), 7.07–
6.70 (m, 3 H), 4.06 (q, J = 7.0 Hz, 2 H), 3.78 (s, 3 H), 1.42 (t, J = 7.0 Hz, 3
H).
13C NMR (50 MHz, CDCl3): δ = 153.9, 146.9, 127.6, 122.6, 120.9, 118.0,
110.8, 64.0, 52.1, 14.7.
The spectra were in accordance with the previously reported data.50
Acknowledgment
This research was supported, in part, by the Ministry of Education
and Science, Republic of Serbia (Grant No. 172032). We thank Dr. Nina
Todorović and Dr. Dejan Godjevac for help with the NMR spectra and
Dr. Milka Jadranin for help with the HPLC/HRMS (Institute of Chemis-
try, Technology and Metallurgy, Department of Chemistry).
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D.; Verhoeven, T. R.; Reider, P. J. J. Am. Chem. Soc. 1994, 116,
7947.
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Chem. 2008, 6, 1849.
(26) The relative stereochemistry of the reactants and products was
reliably estimated from HSQC/NOESY experiments.
tanyl; accessed March 1, 2016.
Supporting Information
Supporting information for this article is available online at
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© Georg Thieme Verlag Stuttgart · New York — Synthesis 2016, 48, A–K