Electric Literature of 127-66-2, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 127-66-2 as follows.
To a solution of alkynol 1b (2.41 g, 2.83 mmol) and azide 2 (1 equiv) in THF/H2O (1/1, 80 mL) were added sodium ascorbate (95.5 mg, 0.48 mmol) and CuSO4*5H2O (60.5 mg, 0.24 mmol). After stirring overnight at ambient temperature, the reaction mixture was diluted with CH2Cl2 and washed with water. The organic phase was dried with MgSO4 and concentrated in vacuo. The residue was purified (flash chromatography, silica gel, 20-50percent gradient EA/PE) to provide 1.11 g (92percent) of alcohol 3b as solid (mp 60-63 °C). 1H NMR (400 MHz, DMSO): delta ppm: 7.85 (s, 1H), 7.63 (dd, 1H, J=7.6, 1.6 Hz), 7.52 (ddd, 1H, J=8.0, 7.6, 2 Hz), 7.45 (m, 2H), 7.28 (m, 2H), 7.20 (m, 1H), 7.11 (d, 1H, J=8.0 Hz), 7.01 (td, 1H, J=7.6, 0.8 Hz), 5.82 (s, 1H), 4.39 (t, 2H, J=7.2 Hz), 4.30 (m, 2H), 4.04 (t, 2H, J=6.0 Hz), 3.57 (m, 2H), 3,.24 (s, 3H), 2.01 (m, 2H), 1.80 (s, 3H), 1.69 (m, 2H); 13C NMR (100 MHz, DMSO): delta ppm: 165.8, 157.5, 155.0, 148.4, 133.5, 130.7, 127.1, 126.1, 125.1, 121.4, 120.15, 120.05, 113.4, 70.9, 69.7, 67.5, 63.4, 58.0, 48.9, 30.8, 26.5, 25.6; HRMS (TOF MS ES+) calcd for [M+Na]+ C29H32N3O5Na: 462.2005, found 462.2000.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,127-66-2, its application will become more common.
Reference:
Article; Delatouche, Regis; Mondon, Martine; Gil, Adri; Frapper, Gilles; Bachmann, Christian; Bertrand, Philippe; Tetrahedron; vol. 67; 2; (2011); p. 401 – 407;,
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