Category: 149057-19-2

149057-19-2, 4-((Benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid is a piperazines compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of piperazine-1,2,4-tricarboxylic acid 4-benzyl ester 1-tert-butyl ester (0.364 g, 1 mmol) in dichloromethane (3 mL) was added O-Methyl Hydroxylamine HCl (95 mg, 1.13 mmol), EDC HCl (0.3 g, 1.57 mmol) and DIEA (0.28 g, 2.17 mmol). The resulting mixture was stirred at room temperature overnight and partitioned between dichloromethane and water. The combined organic extracts were washed with brine, dried, and evaporated. The residue was purified by flash column chromatography on silica gel, eluting with EtOAc/n-Hexane (30/70) to afford the title product.LC/MS (m/z) [M]+ 394.2 (calculated for C19H27N3O6, 393.19).

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

Reference：
Patent; BIGNAN, Gilles; Gaul, Micheal; Xu, Guozhang; Zhao, Bao-Ping; US2011/150864; (2011); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

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.

Stage 1: 4-Benzyl 1 -tert-butyl 2-cyclopentyl piperazi ne-i ,2,4-tricarboxylate 4-[(Benzyloxy)carbonyl]- 1 -(tert-butoxycarbonyl)piperazi ne-2-carboxylic acid (9.96 g, 27 mmol) was dissolved in DCM (50 mL) and cooled to 0CC. Cyclopentanol (7.4 mL, 82 mmol), EDO (7.86 g, 41 mmol) and DMAP (0.33 g, 2.7 mmol) were then added and the reaction allowed to warm to RT, and stirred for 24 hrs. Water (100 mL) and DCM (50 mL) were then added and the layers separated. The aqueous layer was reextracted with DCM (2 x 50 mL) and the combined organic layers were then dried over Mg504 and concentrated in vacuo. Purification by column chromatography (40% EtOAc/heptane) afforded the title compound as a colourless oil (10.4 g, 88%). LCMS: m/z 455 [M+Na]., 149057-19-2

The synthetic route of 149057-19-2 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; CHROMA THERAPEUTICS LTD; DAVIES, Stephen John; PINTAT, Stephane; NORTH, Carl Leslie; MOFFAT, David Festus Charles; WO2014/1802; (2014); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

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;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

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;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

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;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

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;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics