Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 145100-50-1, name is 1,1,1-Trifluoro-N-(pyridin-2-yl)-N-((trifluoromethyl)sulfonyl)methanesulfonamide. A new synthetic method of this compound is introduced below., Computed Properties of C7H4F6N2O4S2
EXAMPLE 2This example illustrates a preparation of abiraterone acetate (I) on an industrial scale starting from prasterone acetate (Ill) according to the invention.51 kg of potassium tert-butylate in THF (760 kg) and prasterone acetate (100 kg) are stirred at a temperature below -70 C. Then N-(2-pyridyl)-bis(trifluoromethanesulfonimide) (1 33 kg) is added maintaining the stirring for 2 hours at a temperature between -70 and -80 C.The cold solution is poured onto a biphasic solution consisting of isopropyl acetate(360 kg) and a 10% ammonium chloride aqueous solution.The phases are separated and the organic phase is first washed with an aqueoussolution of ammonium chloride, then with 450 kg 10% sodium acetate aqueoussolution, and eventually with an aqueous solution of sodium chloride.A part of the solvent is distilled off at reduced pressure obtaining the precipitation of a solid which is eliminated by filtration. The residual solution is then distilled until obtaining an oil which is crystallized from the mixture methanol/triethylamine. The sample obtained after drying (112 kg) verified in HPLC (A = 220 nm) against anauthentic sample is intermediate (II) with 98.14% titer.112 kg of intermediate (II) is dissolved in THF (1079 kg), then bis(triphenylphosphinepalladium(l l)dichloride Pd(P Ph3)2C12 (3.2 kg), diethyl(pyridyl)borane (129.3 kg) and an aqueous solution of sodium carbonate are added under stirring at 20-25 00.Reflux is kept for 1 hour (TLC check), further 400 g of bis(triphenylphosphinepalladium(l l)dichloride Pd(PPh3)2C12 is added, obtaining complete transformation (TLC check) after further 30 minutes of reaction. Cooling down to 20-25 C is performed, the phases are separated by washing the organic phase with an aqueous solution of sodium chloride.The organic phase is then distilled until obtaining a dark oil which is then solubilized with methanol, recovering by fractional crystallization the excess diethyl(pyridyl)borane.Methanol is eliminated by distillation, the residue is dissolved in isopropyl acetate, then the solution is filtered after treatment with decolorising carbon and silica gel.The solution, adjusted at T = 20 ± 5 00 is then treated with oxalic acid dihydrate (60 kg).Stirring is performed at T = 20 ± 5 00 for 8 hours and then the solid is filtered and washed with isopropyl acetate.The abiraterone acetate oxalate obtained is stirred at a temperature between 0 and 500 with methylene chloride (880 kg) and an aqueous solution of sodium bicarbonate.The phases are separated and the organic phase is distilled.The solid obtained is dissolved in isopropyl acetate, then treated with Quadrasil(registered trademark of Johnson Matthey Finland Oy) for 6 hours, for the removal of the catalyst; the Quadrasil scavengers, sold by Sigma-Aldrich, consist of porous silica beads having defined pore size, wherein the silica surface is functionalised with metal binders, and allow a quick and effective removal of traces of metals fromaqueous or organic solutions.After filtration, a part of the solvent is distilled off, cooling down to 0 ± 5 00 is performed obtaining the crystallisation of the product.The abiraterone acetate obtained after drying (65 kg) meets the specifications reported in the corresponding chapter of the European Pharmacopoeia.
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Reference:
Patent; INDUSTRIALE CHIMICA S.R.L.; LENNA, Roberto; DI BRISCO, Riccardo; WO2015/14686; (2015); A1;,
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