Some common heterocyclic compound, 61881-19-4, name is 2,2,2-Trifluoro-N-phenylacetimidoyl chloride, molecular formula is C8H5ClF3N, 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. Quality Control of 2,2,2-Trifluoro-N-phenylacetimidoyl chloride
Compound 16 (97 mg, 42.9 mol) was reacted with (N-phenyl)-2,2,2-trifluoroacetoimidoyl chloride (17.8 mg, 85.8 mol) andK2CO3 (29.7 mg, 215 mol) in acetone (1.7 mL) as described for 13. The crude product was purified bysilica gel column chromatography with hexane-EtOAc (83:17) and gel permeation chromatography[S-X1, toluene-EtOAc (75:25)] to give the title product 17 (94.7 mg, 91%). [alpha]D -35.2 (c 1.3, CHCl3);1H-NMR (500 MHz, CDCl3) delta7.38-7.07 (m, 43H, Ar), 6.82 (d, 1H, J2,NH = 9.4 Hz, NH), 6.71-6.69 (m,2H, Ar), 6.26 (br, 1H, H-1GlcN), 6.00 (d, 1H, J2,NH = 4.7 Hz, NH), 5.88-5.81 (m, 1H, H2C=CHCH2),5.30-5.14 (m, 10H, H2C=CHCH2 2, H-1Fuc 2, H-2Fuc 2, H-3Fuc 2, H-4Fuc 2), 5.07 (d, 1H,J1,2 = 8.1 Hz, H-1GlcN), 5.03-5.00 (m, 2H, H-5Fuc, PhCH2), 4.94 (dd, 1H, J4,5 = 12.7 Hz, J5,6 = 6.4 Hz,H-5Fuc), 4.78 (d, 1H, Jgem = 11.6 Hz, PhCH2), 4.71 (d, 1H, Jgem = 11.2 Hz, PhCH2), 4.63 (d, 1H,Jgem = 11.9 Hz, PhCH2), 4.60-4.37 (m, 13H, PhCH2 11, H-1Gal, H-2GlcN), 4.32 (d, 1H, J1,2 = 7.8 Hz,H-1Gal), 4.20 (t, 1H, J2,3 = J3,4 = 9.2 Hz, H-3GlcN), 4.07-4.01 (m, 3H, H2C=CHCH2 2, H-4GlcN),3.93-3.77 (m, 8H, H-4GlcN, H-2GlcN, H-6aGal, H-6aGal, H-4Gal, H-5GlcN, H-4Gal, H-6bGal), 3.76-3.65(m, 3H, H-3Gal, H-3GlcN, H-2Gal), 3.62-3.52 (m, 5H, H-6aGlcN, H-6bGlcN, H-6aGlcN, H-6bGal, H-2Gal),3.49-3.44 (m, 2H, H-5Gal, H-6bGlcN), 3.38 (dd, 1H, J5,6a = 5.5 Hz, J5,6b = 7.5 Hz, H-5Gal), 3.21-3.18 (m,2H, H-3Gal, H-5GlcN), 2.16 (s, 3H, Ac), 2.15 (s, 3H, Ac), 2.14 (s, 3H, Ac), 2.05 (s, 3H, Ac), 2.01 (s, 6H,Ac 2), 0.85 (d, 3H, H-6Fuc), 0.69 (d, 3H, J5,6 = 6.4 Hz, H-6Fuc); 13C-NMR (125 MHz, CDCl3) delta170.4,170.3, 170.2, 170.1, 169.4, 160.9, 160.7, 142.7, 139.0, 138.8, 138.4, 138.3, 138.2, 138.1, 137.8, 137.6, 137.3,134.9, 129.3, 129.0, 129.0, 128.8, 128.5, 128.4, 128.4, 128.3, 128.2, 128.2, 128.2, 128.1, 128.1, 127.9, 127.8,127.7, 127.7, 127.6, 127.5, 127.3, 127.3, 125.2, 124.6, 119.2, 117.0, 116.6, 114.8, 103.4, 103.2, 99.4, 96.0, 95.6,93.3, 92.6, 92.4, 81.8, 80.8, 78.5, 78.1, 77.6, 76.5, 75.1, 74.9, 74.7, 74.6, 74.4, 74.3, 74.1, 73.4, 73.3, 73.2, 72.9,72.8, 72.4, 72.0, 71.6, 71.5, 71.4, 68.8, 68.5, 68.2, 68.1, 68.0, 67.9, 67.1, 66.7, 64.8, 64.5, 58.7, 54.6, 30.9,29.6, 21.4, 20.9, 20.8, 20.8, 20.7, 20.7, 15.7, 15.2, 14.1. HRMS (ESI) m/z: found [M + Na]+ 2450.6466,C119H130Cl6F3N3O35 calcd. for [M + Na]+ 2450.6466.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 61881-19-4, its application will become more common.
Reference:
Article; Kobayashi, Daisuke; Ueki, Akiharu; Yamaji, Tomoya; Nagao, Kazuya; Imamura, Akihiro; Ando, Hiromune; Kiso, Makoto; Ishida, Hideharu; Molecules; vol. 21; 5; (2016);,
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