New learning discoveries about 4-((Benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid

149057-19-2, As the paragraph descriping shows that 149057-19-2 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.149057-19-2,4-((Benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid,as a common compound, the synthetic route is as follows.

CS2CO3 (0.5 eq) was added to a stirred solution of 4-((benzyloxy)carbonyl)-l-(tert- butoxycarbonyl)piperazine-2-carboxylic acid (1.0 eq) in EtOH (0.54 M) . Stirring was continued at 20 C for 2 h then solvent was evaporated and cesium 4-((benzyloxy)carbonyl)-l-(tert-butoxycarbonyl)-l,4-diazepane-5-carboxylate was dried at high vacuum pump for 1 h, then it was dissolved with DMF (0.54 M) and 2-bromo-l-(naphthalen-2-yl)ethan-l-one (1.0 eq) was added. The mixture was stirred at 20 C for 1 h, then DMF was removed under reduced pressure co- evaporating with toluene. The residue was diluted with EtOAc and filtered off. Filtrate was evaporated to give 4-benzyl 1 -(tert-butyl) 2-(2-(naphthalen-2-yl)-2-oxoethyl) piperazine-1,2,4-tricarboxylate. The latter was dissolved with toluene (0.13 M) and NH4OAc (20 eq) was added. The mixture was stirred at reflux using a Dean Stark apparatus for 30 min. Toluene was removed under reduced pressure, the residue was diluted with EtOAc, washed with sat. aq. NaHC03, brine, dried and concentrated to give an orange oily residue. This material was purified by flash chromatography (petroleum ether/EtOAc from 95:5 to 20:80) to give the title compound (86%) as an orange solid. MS (ES+) m/z 513 (M+H)+.

149057-19-2, As the paragraph descriping shows that 149057-19-2 is playing an increasingly important role.

Reference:
Patent; IRBM SCIENCE PARK S.P.A.; C.N.C.C.S. S.C.A.R.L. COLLEZIONE NAZIONALE DEI COMPOSTI CHIMICI E CENTRO SCREENING; BIANCOFIORE, Ilaria; CIAMMAICHELLA, Alina; FERRIGNO, Federica; HARPER, Steven; MALANCONA, Savina; ONTORIA ONTORIA, Jesus Maria; PAONESSA, Giacomo; PONZI, Simona; SUMMA, Vincenzo; (143 pag.)WO2018/115275; (2018); A1;,
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