Category: 81927-55-1

81927-55-1,Some common heterocyclic compound, 81927-55-1, name is Benzyl 2,2,2-trichloroacetimidate, molecular formula is C9H8Cl3NO, 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 a solution of alcohol 5 (1.00 g, 8.61 mol) and benzyl 2,2,2-trichloroacetimidate26 (4.34 g, 17.2 mmol, 2.0 equiv) in 1,4-dioxane (15 mL) was added trifluoromethanesulfonic acid (0.15 mL, 1.72 mmol, 0.2 equiv) dropwise at room temperature under nitrogen. The reaction was stirred at room temperature for 1.5 h. The mixture was diluted with dichloromethane (35 mL), washed with saturated aqueous solution of sodium bicarbonate (25 mL*2) and brine (25 mL*3), dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography over silica gel (petroleum ether/ethyl acetate 5:1 to 2:1) to afford the titled compound as colorless oil (1.60 g, 90%). The 1H NMR spectrum was identical to literature data. 1H NMR (400 MHz, CDCl3) delta 7.30-7.19 (m, 5H), 4.62-4.54 (m, 1H), 4.56 (d, J=2.9 Hz, 2H), 3.59 and 3.49 (ABX, JAB=10.8 Hz, JAx=3.3 Hz, JBx=4.3 Hz, 2H), 2.59-2.34 (m, 2H), 2.26-2.13 (m, 1H), 2.09-1.97 (m, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Benzyl 2,2,2-trichloroacetimidate, its application will become more common.

Reference:
Article; Yang, Fan; Feng, Liang; Wang, Nengzhong; Liu, Xuge; Li, Jun; Shen, Yuehai; Tetrahedron; vol. 69; 45; (2013); p. 9463 – 9468;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

81927-55-1, These common heterocyclic compound, 81927-55-1, name is Benzyl 2,2,2-trichloroacetimidate, its 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.

A stirred solution of (R)- methyl 3-hydroxy-2-methylpropanoate (9.57 g, 81.0 mmol) and benzyl 2,2,2- trichloroacetimidate (22.50 g, 89.1 mmol) in CH2Cl2 (10 mL) was cooled to 0 0C under N2. Triflic acid (0.1 mL) in CH2Cl2 (1 mL) was added dropwise. After 10 minutes the reaction became a solid mass. After 1 hour, saturated aqueous NaHCO3 was added and the mixture extracted with Et2O. The organics were dried over MgSO4, filtered and concentrated on a rotary evaporator. Hexane was added and the resulting solids collected by vacuum filtration. The filtrate was concentrated on a rotary evaporator and purified using flash chromatography (5-10% EtOAc/hexane) to give 10.39 g (62%) of (R)-methyl 3-(benzyloxy)-2- methylpropanoate as a colorless oil. Rf= 0.20 (10% EtOAc/hexane). 1H NMR (300 MHz, DMSO-D6) delta ppm 1.08 (d, J=7.14 Hz, 3 H) 2.75 (ddd, J=14.01, 12.64, 7.14 Hz, 1 H) 3.44 – 3.59 (m, 2 H) 3.60 (s, 3 H) 4.46 (s, 2 H) 7.23 – 7.40 (m, 5 H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 81927-55-1.

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; WO2007/84560; (2007); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics