79463-77-7,Some common heterocyclic compound, 79463-77-7, name is Diphenyl N-cyanocarbonimidate, molecular formula is C14H10N2O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
To solution of (R)-3-tert-butoxycarbonylaminopipiridine (154.0 g, 0.769 mol) in iPrOH (3.0 L) was added diphenyl cyanocarbonimidate (183.2 g, 0.769 mol). The mixture was stirred at room temperature for 2.5 h. To the reaction mixture was added glycine ethyl ester¡¤hydrochloride (536.7 g, 3.85 mol) at 0 C, and the mixture was stirred at 80 C for 6 h. After cooling to room temperature, the reaction mixture was diluted with AcOEt (1.4 L) and the precipitate was removed by filtration through a Celite pad. The filtrate was concentrated in vacuo, and the residue was diluted with 5% sodium carbonate solution and extracted with CHCl3 three times. The combined organic layers were dried over Na2SO4, and concentrated in vacuo. The residue was purified by silica-gel column chromatography to give 7 (249.2 g, yield 92%) as a pale yellow oil. 1H NMR (300 MHz, CDCl3) delta 5.68 (br s, 1H), 4.66 (br s, 1H), 4.28-4.19 (m, 4H), 3.81-3.34 (m, 5H), 2.05-1.51 (m, 4H), 1.45 (s, 9H), 1.30 (t, J=7.2 Hz, 3H); 13C NMR (75 MHz, CDCl3) delta 169.6, 160.0, 155.5, 117.1, 80.1, 61.8, 51.2, 47.3, 45.4, 44.6, 29.8, 28.3, 22.8, 14.1; HRMS (ESI) [M+H]+ calcd for C16H28N5O4 354.2136, found 354.2128; IR (ATR): 1743, 1685, 1575, 1531, 1440, 1390, 1365, 1309, 1243, 1197, 1162, 1051, 1031, 1018 cm-1.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Diphenyl N-cyanocarbonimidate, its application will become more common.
Reference:
Article; Ikuma, Yohei; Nakahira, Hiroyuki; Tetrahedron; vol. 67; 49; (2011); p. 9509 – 9517;,
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