1746-77-6, These common heterocyclic compound, 1746-77-6, name is Isopropyl carbamate, 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.
Intermediate 491 -methylethyl (2E)-2-butenoylcarbamateIsopropyl carbamate (30 g, 291 mmol, available from TCI) was charged to a 3L Lara vessel and dry Tetrahydrofuran (THF) (150 ml) added. (2E)-2-butenoyl chloride (31.2 ml, 326 mmol, available from Aldrich) was added under nitrogen and the jacket cooled to – 30C. When the solution temperature reached -17C 1 M Lithium tert-butoxide (655 ml, 655 mmol) was added by peristaltic pump over 2 hours, keeping the reaction temperature between -10C and -18C. Once the addition was complete the mixture was complete the mixture was stirred for 30 mins and brought to 0C. Diethyl ether (450ml) and 1 M HCI (375ml) were added and the mixture brought to 20C with vigourous stirring. The stirring was stopped, the layers allowed to separate and the aqueous layer run off. Brine (375ml) was added and the mixture stirred vigourously. The stirring was stopped, the layers allowed to separate and the aqueous layer run off. The organic layer was dried (magnesium sulfate), filtered and evaporated to a brown oil (60g). The mixture was loaded on to a 40+M Biotage silica column and eluted with DCM:ethyl acetate (1 :1 to 0:1 , 10CV). The product containing fractions were evaporated to dryness and loaded on to a 1500g Redisep Isco silica column and eluted with a gradient of 0 to 40% ethyl acetate in cyclohexane. The clean, product containing fractions were evaporated to an off white solid (15.41 g). LCMS (Method C): Rt = 0.68 , MH+ = 172
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 1746-77-6.
Reference:
Patent; GLAXOSMITHKLINE LLC; DEMONT, Emmanuel, Hubert; GARTON, Neil, Stuart; GOSMINI, Romain, Luc, Marie; HAYHOW, Thomas, George, Christopher; SEAL, Jonathan; WILSON, David, Matthew; WOODROW, Michael, David; WO2011/54841; (2011); A1;,
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