Analyzing the synthesis route of 81927-55-1

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.

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