Adding a certain compound to certain chemical reactions, such as: 61881-19-4, name is 2,2,2-Trifluoro-N-phenylacetimidoyl chloride, belongs to chlorides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 61881-19-4, HPLC of Formula: C8H5ClF3N
To a solution of the hemiacetal 28 in acetone (10mL) and water (50muL), Cs2CO3 (189mg, 0.6mmol) and (N-phenyl)trifluoroacetimidoyl chloride (56muL, 0.4mmol) were added at room temperature. The reaction mixture was stirred for 3h at room temperature. After complete reaction (monitored by TLC), the mixture was filtered through Celite by elution with chloroform. The combined filtrates were concentrated and purified by flash chromatography (solvent D) to yield compound 29 (236mg, 87%) as a colorless foam: [alpha]D23 +164.2 (c 0.3, CHCl3); Rf=0.57 (solvent B2); 1H NMR (500.13MHz, CDCl3): delta 8.08 (m, 2H), 7.97 (m, 2H), 7.81 (m, 2H), 7.61-7.56 (m, 4H), 7.49-7.42 (m, 4H), 7.41-7.08 (m, 22H), 7.05 (m, 2H), 6.83 (m, 2H) (4 CH2C6H5, 3 COC6H5, NC6H5); 6.27 (br, 1H, H-1); 5.93 (dd, 1H, 3J2?,3?=10.7Hz, 3J3?,4?=3.5Hz, H-3?); 5.78 (dd, 1H, 3J2,3=3.0Hz, 3J1,2=2.0Hz, H-2); 5.58 (dd, 1H, 3J3?,4?=3.5Hz, 3J4?,5?=1.4Hz, H-4?); 5.46 (d, 1H, 3J1?,2?=3.3Hz, H-1?); 5.07 (dd, 1H, 3J2?,3?=3.3Hz, 3J1?,2?=1.9Hz, H-2?); 5.08, 4.94 (2d, 2H, 2J=10.4Hz, CH2C6H5); 4.89 (d, 1H, 3J1?,2?=1.9Hz, H-1?); 4.74, 4.58 (2d, 2H, 2J=11.4Hz, CH2C6H5); 4.68 (m, 1H, H-5?); 4.55 (dd, 1H, 3J3,4=9.8Hz, 3J2,3=3.0Hz, H-3); 4.50 (dd, 1H, 3J2?,3?=10.7Hz, H-2?); 4.24 (center of qAB, 2H, 2J=12.2Hz), 4.15, 3.43 (2d, 2H, 2J=10.7Hz), (2 CH2C6H5); 4.03 (dq, 1H, 3J4,5=9.2Hz, 3J5,6=6.1Hz, H-5); 3.98 (dq, 1H, 3J4?,5?=9.1Hz, 3J5?,6?=6.3Hz, H-5?); 3.98 (?t?, 1H, 3J3,4=9.8Hz, 3J4,5=9.5Hz, H-4); 3.43 (dd, 1H, 3J5?,6a?=6.3Hz, H-6a?); 3.31 (dd, 1H, 2J6a?,6b?=10.2Hz, 3J5?,6b?=5.7Hz, H-6b?); 3.26 (dd, 1H, 3J3?,4?=8.8Hz, 3J2?,3?=3.3Hz, H-3?); 3.23 (?t?, 1H, 3J4?,5?=9.1Hz, H-4?); 1.63 (s, 3H, COCH3); 1.54 (d, 3H, 3J5,6=6.1Hz, H-6); 1.39 (d, 3H, 3J5?,6?=6.3Hz, H-6?); 13C NMR (125.8MHz, CDCl3): delta 168.8 (COCH3); 165.1, 165.2, 165.5 (3 COC6H5); 143.2 (i-NC6H5); 137.4, 137.8, 138.2, 138.9 (4 i-CH2C6H5); 133.4, 133.3, 133.0 (3 p-COC6H5); 130.6-127.2 (several signals of o-, m-COC6H5, o-, m-, p-CH2C6H5, m-NC6H5); 129.5, 129.3, 128.8 (3 i-COC6H5); 124.4 (p-NC6H5); 119.4 (o-NC6H5); 115.9 (q, 1JC,F=287Hz, CF3); 100.0 (C-1?); 94.4 (C-1?); 93.7 (br, C-1); 79.9 (C-4?); 79.0 (C-4); 77.8 (C-3?); 76.3, 75.0, 72.8, 71.2 (4 CH2C6H5); 71.7 (C-2?); 71.5 (C-3); 71.3 (C-5); 70.8 (C-3?); 69.8 (C-4?); 68.5 (C-5?); 68.4 (C-2?); 67.8 (C-6?); 67.3 (C-5?); 66.7 (C-2); 20.3 (COCH3); 18.4 (C-6); 18.1 (C-6?); CCF3 signal not given; 19F NMR (282.4MHz, CDCl3): delta -75.7 (CF3). HRMS (ESI-TOF): calcd for C77H74F3NO18 (M+Na+): m/z 1380.4750, found: m/z 1380.4751.
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2,2,2-Trifluoro-N-phenylacetimidoyl chloride, other downstream synthetic routes, hurry up and to see.
Reference:
Article; Nilsson, Inga; Michalik, Dirk; Silipo, Alba; Molinaro, Antonio; Vogel, Christian; Carbohydrate Research; vol. 404; (2015); p. 98 – 107;,
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