H
V. Kumar et al.
Paper
Synthesis
1H NMR (300 MHz, CDCl3): δ = 7.21–7.12 (m, 5 H), 5.35 (br d, J = 8.7
Hz, 1 H), 4.52–4.49 (m, 1 H), 3.38–3.20 (m, 3 H), 2.92–2.83 (m, 2 H),
2.52–2.47 (m, 1 H), 1.70–1.49 (m, 4 H), 1.34 (s, 9 H).
J. W. Nature 2011, 480, 471. (j) Roughley, S. D.; Jordan, A. M.
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Functional Group Transformations: Synthesis: Carbon with One
tert-Butyl {1-[(2-Morpholinophenyl)amino]-1-oxo-3-phenylpro-
pan-2-yl}carbamate (15b)
The title compound was prepared following the general procedure for
nucleophilic acyl substitution, from the corresponding carboxylic
acid anhydride and 2-morpholinoaniline; white solid; yield: 357 mg
(84%); mp 121–124 °C.
Heteroatom Attached by a Single Bond;2Vo.
l
Katritzky, A. R.; Ley, S. V.;
Meth-Cohn, O.; Rees, C. W., Eds.; Elsevier: Amsterdam, 1995.
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IR (neat): 3308, 2960, 1715, 1659, 1518 cm-1
1H NMR (300 MHz, CDCl3): δ = 8.92 (br s, 1 H), 8.45 (d, J = 8.4 Hz, 1 H),
7.29–7.10 (m, 8 H), 5.04 (br s, 1 H), 4.51 (br s, 1 H), 3.70–3.69 (m, 4 H),
3.20 (t, J = 6 Hz, 2 H), 2.67–2.61 (m, 4 H), 1.43 (s, 9 H).
13C NMR (75 MHz, CDCl3): δ = 169.1, 155.1, 140.9, 136.5, 132.9, 129.4,
128.8, 127.0, 125.7, 124.1, 120.6, 119.3, 67.4, 52.3, 38.5, 28.3.
HRMS (APCI): m/z [M + H]+ calcd for C24H32N3O4: 426.2317; found:
426.2433.
(3) (a) Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry: Part
A: Structure and Mechanisms; Springer: Berlin, 2007. (b) Das, R.;
Chakraborty, D. Synthesis 2011, 1621. (c) Sakakura, A.; Kawajiri,
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tert-Butyl [4-(Azidocarbonyl)phenyl]carbamate (16b)
The title compound was prepared following the general procedure for
nucleophilic acyl substitution, from the corresponding benzoic anhy-
dride and sodium azide; white solid; yield: 206 mg (79%); mp 124–
127 °C.
(4) (a) Liu, Y.; Liu, R.; Szostak, M. Org. Biomol. Chem. 2017, 15, 1780.
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54, 36. (g) Nangia, A.; Chandrasekaran, S. J. Chem. Res., Synop.
1984, 100.
IR (neat): 3344, 2138, 1728, 1670 cm-1
1H NMR (300 MHz, CDCl3): δ = 7.97–7.93 (m, 2 H), 7.46 (d, J = 7.2 Hz, 2
H), 6.79 (br s, 1 H), 1.52 (s, 9 H).
13C NMR (75 MHz, CDCl3): δ = 171.6, 152.0, 144.1, 131.0, 124.8, 117.4,
81.5, 28.2.
MS (APCI): m/z = 133.1 [M – (Boc + N2)]+.
(5) (a) Huang, P.-Q.; Huang, Y.-H.; Geng, H.; Ye, J.-L. Sci. Rep. 2016, 6,
28801. (b) Huang, P.-Q.; Huang, Y.-H.; Xiao, K.-J. J. Org. Chem.
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Acknowledgment
We would like to thank THSTI (Translational Health Science and Tech-
nology Institute) for intramural research funding.
Supporting Information
Supporting information for this article is available online at
S
u
p
p
ortioInfgrmoaitn
S
u
p
p
ortiInfogrmoaitn
(6) See the Supporting Information for all experimental details and
analytical data.
(7) (a) King, J. F.; Harding, D. R. K. Can. J. Chem. 1976, 54, 2652.
(b) King, J.; Durst, T. J. Am. Chem. Soc. 1964, 86, 287. (c) Opitz, G.;
Adolph, H. Angew. Chem., Int. Ed. Engl. 1962, 1, 113.
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© Georg Thieme Verlag Stuttgart · New York — Synthesis 2018, 50, A–I