Category: 138775-02-7

138775-02-7, (R)-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

PREPARATIVE EXAMPLE 5; The title compound from Prepartive Example 4 (9.6 gm, 26.3 mmol) was dissolved in absoluteEtOH (100 mL) in a hydrogenation vessel. The vessel was flushed with N2 and 10% Pd/C (3.0g, 50% by weight with water) was added. The mixture was hydrogenated at 55 psi of H2 for 18 hours during which time a precipitate formed. When the reaction was complete (TLC, 30% MeOH/NH3/CH2Cl2), the reaction mixture was filtered through a pad of celite, and the pad washed with EtOH followed by distilled H2O. The filtrate was evaporated to ?1/3 the volume and distilled H2O (200 mL) was added. The resulting solution was extracted with EtOAc (contains pure N,N-Di-Boc-2-carboxy-piperazine which was saved). The water layer was evaporated to dryness with azeotropic removal of residual H2O with methanol (2X) to give pure product (3.98g)., 138775-02-7

The synthetic route of 138775-02-7 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; SCHERING CORPORATION; EP1140904; (2005); B1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

138775-02-7, (R)-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

PREPARATIVE EXAMPLE 5; The title compound from Prepartive Example 4 (9.6 gm, 26.3 mmol) was dissolved in absoluteEtOH (100 mL) in a hydrogenation vessel. The vessel was flushed with N2 and 10% Pd/C (3.0g, 50% by weight with water) was added. The mixture was hydrogenated at 55 psi of H2 for 18 hours during which time a precipitate formed. When the reaction was complete (TLC, 30% MeOH/NH3/CH2Cl2), the reaction mixture was filtered through a pad of celite, and the pad washed with EtOH followed by distilled H2O. The filtrate was evaporated to ?1/3 the volume and distilled H2O (200 mL) was added. The resulting solution was extracted with EtOAc (contains pure N,N-Di-Boc-2-carboxy-piperazine which was saved). The water layer was evaporated to dryness with azeotropic removal of residual H2O with methanol (2X) to give pure product (3.98g)., 138775-02-7

The synthetic route of 138775-02-7 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; SCHERING CORPORATION; EP1140904; (2005); B1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

138775-02-7, (R)-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

(2i?)-4-[(Benzyloxy)carbonyl]-l-(tert-butoxycarbonyl)piperazine-2-carboxylic acid (1.4 g, 3.9 mmol) was dissolved in dimethoxyethane (10 mL) and to the cooled resultant solution was added N-methylmorpholine (0.4 g, 3.9 mmol) followed by isobutyl chloroformate (0.54 g, 3.9 mmol) by means of drops. The mixture was stirred at 0C for 20 min and then the mixture was filtered. The filtrate was transferred to a 500 mL flask and then cooled again. Sodium borohydride (0.22 g, 5.9 mmol) dissolved in water (5 mL) was added and the external cooling bath was removed. The reaction mixture was stirred until the temperature of it had reached RT whereupon water (120 mL) was added. The mixture was extracted trice with ethyl acetate and the combined organic solutions were dried and then evaporated. The product was purified by column chromatography on silica gel (ethyl acetate – heptane 10% to 70%). There was obtained 1.2 g (84%) of 4-benzyl 1-tert-butyl (2i?)-2-(hydroxymethyl)piperazine-l,4-dicarboxylate as a colorless oil. 1HNMR (500 MHz, CDCl3): 1.4 (s, 9H), 2.7-3.2 (b, 4H), 3.5 (b, 2H), 3.8-4.2 (m, 4H), 5.1 (m, 2H)5 7.2- 7.4 (m, 5H); LCMS: m/z 349 (M-I)

138775-02-7, 138775-02-7 (R)-4-((Benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid 7010654, apiperazines compound, is more and more widely used in various fields.

Reference：
Patent; ASTRAZENECA AB; WO2007/37743; (2007); 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.138775-02-7,(R)-4-((Benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid,as a common compound, the synthetic route is as follows.

(2,S)-4-Benzyloxycarbonyl-l-/er/-butoxycarbonyl-piperazine-2-carboxylic acid (5.0 g, 13.72 mmol) was dissolved in anhydrous THF (70 mL) and cooled to 0 C with an ice bath. Borane dimethyl sulfide complex (2.6 mL, 27.44 mmol) was added dropwise at 0 C, slowly. Then the reaction solution was left to warm up to room temperature and stirred overnight. The reaction mixture was then cooled to 0 C with an ice bath and quenched with water, dropwise, and extracted with EtOAc. The aqueous phase was extracted with DCM (2x). Combined organic layers were dried over anhydrous MgS04, filtered and evaporated under reduced pressure. It was used without further purification.

138775-02-7, The synthetic route of 138775-02-7 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; EMORY UNIVERSITY; LIOTTA, Dennis C.; JECS, Edgars; ALTAS TAHIROVIC, Yesim; WILSON, Lawrence; PELLY, Stephen Christopher; (102 pag.)WO2019/183133; (2019); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

138775-02-7, (R)-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

(2/?)-4-[(benzyloxy)carbonyl]-1 -[(ferf-butoxy)carbonyl]piperazine-2-carboxylic acid (4.00 g, 1 1.0 mmol), DIPEA (5.1 ml_, 27.4 mmol), HATU (5.01 g, 13.2 mmol) and N,0- dimethylhydroxylamine hydrochloride (1.29 g, 13.2 mmol) in DMA (40 ml.) are stirred at rt over the weekend. The reaction mixture is diluted with EtOAc, and washed with water and brine. The organic layer is dried over MgS04, filtered, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (EtOAc/heptane) to afford the title compound. (0734) Yield: 4.44 g (99%) ESI-MS: m/z = 408 (M+H)+, 138775-02-7

The synthetic route of 138775-02-7 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HYDRA BIOSCIENCES, INC.; BRUNETTE, Steven; CUI, Jianwen; LOWE, Michael D.; SARKO, Christopher Ronald; SURPRENANT, Simon; TURNER, Michael Robert; WU, Xinyuan; SMITH KEENAN, Lana Louise; BOUYSSOU, Thierry; (183 pag.)WO2019/158572; (2019); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

138775-02-7, (R)-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

(2/?)-4-[(benzyloxy)carbonyl]-1 -[(ferf-butoxy)carbonyl]piperazine-2-carboxylic acid (4.00 g, 1 1.0 mmol), DIPEA (5.1 ml_, 27.4 mmol), HATU (5.01 g, 13.2 mmol) and N,0- dimethylhydroxylamine hydrochloride (1.29 g, 13.2 mmol) in DMA (40 ml.) are stirred at rt over the weekend. The reaction mixture is diluted with EtOAc, and washed with water and brine. The organic layer is dried over MgS04, filtered, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (EtOAc/heptane) to afford the title compound. (0734) Yield: 4.44 g (99%) ESI-MS: m/z = 408 (M+H)+, 138775-02-7

The synthetic route of 138775-02-7 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HYDRA BIOSCIENCES, INC.; BRUNETTE, Steven; CUI, Jianwen; LOWE, Michael D.; SARKO, Christopher Ronald; SURPRENANT, Simon; TURNER, Michael Robert; WU, Xinyuan; SMITH KEENAN, Lana Louise; BOUYSSOU, Thierry; (183 pag.)WO2019/158572; (2019); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics

138775-02-7, (R)-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

(2i?)-4-[(Benzyloxy)carbonyl]-l-(tert-butoxycarbonyl)piperazine-2-carboxylic acid (1.4 g, 3.9 mmol) was dissolved in dimethoxyethane (10 mL) and to the cooled resultant solution was added N-methylmorpholine (0.4 g, 3.9 mmol) followed by isobutyl chloroformate (0.54 g, 3.9 mmol) by means of drops. The mixture was stirred at 0C for 20 min and then the mixture was filtered. The filtrate was transferred to a 500 mL flask and then cooled again. Sodium borohydride (0.22 g, 5.9 mmol) dissolved in water (5 mL) was added and the external cooling bath was removed. The reaction mixture was stirred until the temperature of it had reached RT whereupon water (120 mL) was added. The mixture was extracted trice with ethyl acetate and the combined organic solutions were dried and then evaporated. The product was purified by column chromatography on silica gel (ethyl acetate – heptane 10% to 70%). There was obtained 1.2 g (84%) of 4-benzyl 1-tert-butyl (2i?)-2-(hydroxymethyl)piperazine-l,4-dicarboxylate as a colorless oil. 1HNMR (500 MHz, CDCl3): 1.4 (s, 9H), 2.7-3.2 (b, 4H), 3.5 (b, 2H), 3.8-4.2 (m, 4H), 5.1 (m, 2H)5 7.2- 7.4 (m, 5H); LCMS: m/z 349 (M-I)

138775-02-7, As the paragraph descriping shows that 138775-02-7 is playing an increasingly important role.

Reference：
Patent; ASTRAZENECA AB; WO2007/37743; (2007); 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.138775-02-7,(R)-4-((Benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid,as a common compound, the synthetic route is as follows.

(2R)-4-[(benzyloxy)carbonyl]-1 -[(ie f-butoxy)carbonyl]piperazine-2-carboxylic acid (4.00 g, 1 1 .0 mmol), DIPEA (5.1 mL, 27.4 mmol), HATU (5.01 g, 13.2 mmol) and Nu,Omicron- dimethylhydroxylamine hydrochloride (1.29 g, 13.2 mmol) in DMA (40 mL) are stirred at RT for 3 days. The reaction mixture is diluted with EtOAc, washed with water and brine. The organic layer is dried over MgS04, filtered and concentrated under reduced pressure. The residue is purified by silica gel column chromatography to give the title compound. (0523) Yield: 4.44 g (99%) ESI-MS: m/z = 408 (M+H)+

138775-02-7, As the paragraph descriping shows that 138775-02-7 is playing an increasingly important role.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HYDRA BIOSCIENCES, INC.; BOUYSSOU, Thierry; GOTTSCHLING, Dirk; HEINE, Niklas; SMITH KEENAN, Lana Louise; LOWE, Michael D.; RAZAVI, Hossein; SARKO, Christopher Ronald; SURPRENANT, Simon; TAKAHASHI, Hidenori; TURNER, Michael Robert; WU, Xinyuan; (182 pag.)WO2019/81637; (2019); A1;,
Piperazine – Wikipedia
Piperazines – an overview | ScienceDirect Topics