New learning discoveries about 485-71-2

485-71-2, 485-71-2 Cinchonidine 101744, acatalyst-ligand compound, is more and more widely used in various fields.

485-71-2, Cinchonidine is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

The modification of CD and the subsequent later hydroxylationwere performed as reported in our previous works [26,27]. Briefly,an ice-cooled solution of CD in THF containing TEA was added drop-wise to the TMCS. The reaction mixture was stirred for 20 h at roomtemperature and then for 2 h at 60C. The product was extractedwith chloroform and washed with water. The obtained productwas hydrosilated with the Pt(COD)Cl2catalyst precursor and TMS(TMS/catalyst = 120 mol ratio) at 40C, using toluene as the sol-vent. The reaction mixture was stirred for 5 h at 90C under a N2atmosphere. Purification was performed by flash chromatography(hexane-acetone-TEA = 40:18:1).

485-71-2, 485-71-2 Cinchonidine 101744, acatalyst-ligand compound, is more and more widely used in various fields.

Reference£º
Article; Campos, Cristian H.; Torres, Cecilia C.; Osorio-Vargas, Paula; Mella, Claudio; Belmar, Julio; Ruiz, Doris; Fierro, Jose L.G.; Reyes, Patricio; Journal of Molecular Catalysis A: Chemical; vol. 398; (2015); p. 190 – 202;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

Downstream synthetic route of 485-71-2

485-71-2, 485-71-2 Cinchonidine 101744, acatalyst-ligand compound, is more and more widely used in various fields.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.485-71-2,Cinchonidine,as a common compound, the synthetic route is as follows.

General procedure: The alkaloid (12.3 mmol, 1 eq.) and the appropriate substituted benzylic halide derivative(12.3 mmol, 1 eq.) were dissolved in THF (40 mL) with addition of a trace of NaI. The mixture washeated to reflux overnight and then cooled and stirred at ambient temperature for 1 h. In most cases theproduct precipitated as an off-white solid, but where this was not the case and the mixture containedonly a small amount of solid or no solid at all, then diethyl ether (20 mL) was added dropwise.The solid was removed via filtration and washed with THF (50 mL) or ether:THF, (1:1, v/v, 50 mL)and was dried under reduced pressure at 40 C. Where the solid formed was not a fine powder it was then taken up in DCM and this solution was then added dropwise to rapidly stirring ether (100 mL).This usually gives a finely divided solid that could be filtered and dried. (Note: The cinchonine derivedPTCs are usually very insoluble. The quinidine derived PTCs are often completely soluble at the endof the reaction.) The di(t-butyl)benzyl PTC was prepared according to the standard procedure aboveand was filtered directly from the reaction mixture.

485-71-2, 485-71-2 Cinchonidine 101744, acatalyst-ligand compound, is more and more widely used in various fields.

Reference£º
Article; Zhang, Tao; Scalabrino, Gaia; Frankish, Neil; Sheridan, Helen; Molecules; vol. 23; 7; (2018);,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

Some tips on 485-71-2

485-71-2, The synthetic route of 485-71-2 has been constantly updated, and we look forward to future research findings.

485-71-2, Cinchonidine is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step B1: (9R)-1-[3,5-Bis(trifluoromethyl)benzyl]cinchonan-1-ium-9-ol bromide [table-us-00013-en] d Materials FW Mass Volume mol Equiv. (g/mL) Cinchonidine 294.39 6.1 kg 20.72 1 3,5-Bis(trifluoro-methyl)benzylbromide 307.03 7.0 kg 4.19 L 22.8 1.1 1.671 IPA 66 L (0217) 3,5-Bis(trifluoromethyl)benzyl bromide (7.0 kg) was dissolved in isopropyl alcohol (IPA, 60 L) at 23 C. under nitrogen. To the stirred light yellow solution was added cinchonidine (6.1 kg) in portions over 20 minutes (no exotherm), affording a white slurry. Additional IPA (6 L) was added to rinse all the cinchonidine down into the reaction mixture. The slurry was heated to gentle reflux, reaching an internal temperature of 80-82.5 C. The mixture became less viscous while being heated, and once the temperature had reached 60.6 C. the last of the cinchonidine had dissolved to give a dark yellow solution. Once the mixture had reached gentle reflux, the reaction was seeded by the addition of (9R)-1-[3,5-Bis(trifluoromethyl)benzyl]cinchonan-1-ium-9-ol bromide (62.3 g, 0.104 mol, 0.5 mol % relative to cinchonidine starting material), which led to the immediate precipitation of the product. The mixture was maintained at gentle reflux for 3.5 h, then heating was ceased and the orange slurry was allowed to cool to room temperature (21 C.) with stirring overnight. (0218) After cooling, the mixture was filtered, and the pink product cake was washed with fresh IPA (1¡Á10 L then 1¡Á30 L) to remove unreacted starting materials and most of the color, and dried under vacuum with a nitrogen sweep to afford the title product.

485-71-2, The synthetic route of 485-71-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Merck Sharp & Dohme Corp.; Bell, Ian M.; Fraley, Mark; Gallicchio, Steven N.; Ginnetti, Anthony; Mitchell, Helen J.; Paone, Daniel V.; Staas, Donnette D.; Wang, Cheng; Zartman, C. Blair; Stevenson, Heather E.; (30 pag.)US9499541; (2016); B2;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

Simple exploration of 485-71-2

The synthetic route of 485-71-2 has been constantly updated, and we look forward to future research findings.

485-71-2,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.485-71-2,Cinchonidine,as a common compound, the synthetic route is as follows.

4-Hydroxyphenylacetic acid (40 mg, 0.263 mmol) and cinchonidine (77.4 mg, 0.263 mmol) were dissolved in isopropanol (IPA). The solution was left to evaporate and crystals were obtained after one week

The synthetic route of 485-71-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Amombo Noa, Francoise M.; Jacobs, Ayesha; Journal of Molecular Structure; vol. 1114; (2016); p. 30 – 37;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

Some tips on 485-71-2

485-71-2, The synthetic route of 485-71-2 has been constantly updated, and we look forward to future research findings.

485-71-2, Cinchonidine is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: A mixture of 2 or 3 (0.50 mmol), the corresponding acids RCOOH (0.60 mmol),DCC (0.60 mmol), DMAP (0.1 mmol) in dry dichloromethane (15 mL) was stirred atroom temperature. When the reaction was completed, and checked by TLC, the mixturewas filtered to remove urea from the reaction, and the filtrate was diluted bydichloromethane (45 mL). Subsequently, the diluted organic phase was washed bysaturated aqueous NaHCO3 (30 mL), and brine (30 mL), dried over anhydrousNa2SO4, concentrated in vacuo, and purified by CC to give the pure 9R/S-acyloxyderivatives of cinchonidine and cinchonine 5a-j,l-o and 6a,c,e-o [17-19]. The dataof target compounds are shown as follows.

485-71-2, The synthetic route of 485-71-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Che, Zhi-Ping; Chen, Gen-Qiang; Jiang, Jia; Lin, Xiao-Min; Liu, Sheng-Ming; Sun, Di; Tian, Yue-E; Yang, Jin-Ming; Zhang, Song; Journal of Asian Natural Products Research; (2020);,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

Analyzing the synthesis route of 485-71-2

As the paragraph descriping shows that 485-71-2 is playing an increasingly important role.

485-71-2, Cinchonidine is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,485-71-2

Example 11 (R)-1-(2-Hydroxyethyl)-4-methyl-5-[2-(trifluoromethyl)phenyl]-1H-pyrrole-3-carboxylic acid cinchonidine salt To cinchonidine (46.98 g (159.6 mmol)), ethyl acetate (1400 mL) was added, and while heating and stirring the resulting mixture under reflux (about 78 C.), (RS)-1-(2-hydroxyethyl)-4-methyl-5-[2-(trifluoromethyl)phenyl]-1H-pyrrole-3-carboxylic acid (50.00 g (159.6 mmol)) was added thereto. The resulting mixture was stirred for about 1 hour, and then gradually cooled to 20 to 30 C., and further stirred for about 1 hour at that temperature. The deposited crystal was filtered and washed with ethyl acetate (250 mL). The obtained wet crystal product was dried under reduced pressure at 40 C., whereby a crude product of the title compound (52.73 g) was obtained (yield: 54.4%). The diastereomeric excess of the obtained salt was 71.9% de. To the obtained crude product (50.00 g), ethanol (75 mL) and ethyl acetate (100 mL) were added, and the resulting mixture was heated and stirred under reflux (about 78 C.). After the mixture was stirred for about 1 hour, ethyl acetate (825 mL) was added thereto, and the resulting mixture was stirred under reflux again for about 0.5 hours. Thereafter, the mixture was cooled to 0 to 5 C. and stirred for about 1 hour at that temperature. The resulting crystal was filtered and washed with ethyl acetate (200 mL) cooled to 0 to 5 C. The obtained wet crystal product was dried under reduced pressure at 40 C., whereby the title compound was obtained (34.21 g, recovery rate: 68.4%, yield: 37.2%). The diastereomeric excess of the obtained salt was 98.7% de. 1H NMR (400 MHz, CDCl3) delta: 1.27-1.67 (m, 2H), 1.75-2.04 (m, 4H), 2.13-2.33 (m, 1H), 2.52-2.94 (m, 2H), 3.14-3.23 (m, 2H), 3.46-4.12 (m, 2H), 4.76-5.10 (m, 2H), 5.58-5.90 (m, 2H), 6.10-6.95 (m, 2H), 7.00-8.25 (m, 7H), 8.55-9.01 (m, 1H). MS (ESI): 313, 294

As the paragraph descriping shows that 485-71-2 is playing an increasingly important role.

Reference£º
Patent; Daiichi Sankyo Company, Limited; Watanabe, Masashi; Okachi, Takahiro; Kawahara, Michiaki; Nagasawa, Hiroshi; Sato, Noritada; Takita, Takashi; Hasegawa, Gen; (23 pag.)US2016/96803; (2016); A1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

New learning discoveries about 485-71-2

485-71-2, 485-71-2 Cinchonidine 101744, acatalyst-ligand compound, is more and more widely used in various fields.

485-71-2, Cinchonidine is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: A mixture of 2 or 3 (0.50 mmol), the corresponding acids RCOOH (0.60 mmol),DCC (0.60 mmol), DMAP (0.1 mmol) in dry dichloromethane (15 mL) was stirred atroom temperature. When the reaction was completed, and checked by TLC, the mixturewas filtered to remove urea from the reaction, and the filtrate was diluted bydichloromethane (45 mL). Subsequently, the diluted organic phase was washed bysaturated aqueous NaHCO3 (30 mL), and brine (30 mL), dried over anhydrousNa2SO4, concentrated in vacuo, and purified by CC to give the pure 9R/S-acyloxyderivatives of cinchonidine and cinchonine 5a-j,l-o and 6a,c,e-o [17-19]. The dataof target compounds are shown as follows.

485-71-2, 485-71-2 Cinchonidine 101744, acatalyst-ligand compound, is more and more widely used in various fields.

Reference£º
Article; Che, Zhi-Ping; Chen, Gen-Qiang; Jiang, Jia; Lin, Xiao-Min; Liu, Sheng-Ming; Sun, Di; Tian, Yue-E; Yang, Jin-Ming; Zhang, Song; Journal of Asian Natural Products Research; (2020);,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

Downstream synthetic route of 485-71-2

485-71-2 Cinchonidine 101744, acatalyst-ligand compound, is more and more widely used in various fields.

485-71-2,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.485-71-2,Cinchonidine,as a common compound, the synthetic route is as follows.

General procedure: A mixture of (-)-cinchonidine (1.0 mmol) and benzyl bromide 3 (1.0 mmol) having sulfonamidegroup was stirred in DMF (4 mL) at 25 C for 20 h. After the reaction was completed, the reaction mixture was added dropwise to ether (50mL) with stirring. The solid precipitated was filtered,washed with ether (20 mL) and hexane (20 mL) to afford cinchonidinium salt 5

485-71-2 Cinchonidine 101744, acatalyst-ligand compound, is more and more widely used in various fields.

Reference£º
Article; Itsuno, Shinichi; Yamamoto, Shunya; Takata, Shohei; Tetrahedron Letters; vol. 55; 44; (2014); p. 6117 – 6120;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

Some tips on 485-71-2

The synthetic route of 485-71-2 has been constantly updated, and we look forward to future research findings.

485-71-2,485-71-2, Cinchonidine is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: The alkaloid (12.3 mmol, 1 eq.) and the appropriate substituted benzylic halide derivative(12.3 mmol, 1 eq.) were dissolved in THF (40 mL) with addition of a trace of NaI. The mixture washeated to reflux overnight and then cooled and stirred at ambient temperature for 1 h. In most cases theproduct precipitated as an off-white solid, but where this was not the case and the mixture containedonly a small amount of solid or no solid at all, then diethyl ether (20 mL) was added dropwise.The solid was removed via filtration and washed with THF (50 mL) or ether:THF, (1:1, v/v, 50 mL)and was dried under reduced pressure at 40 C. Where the solid formed was not a fine powder it was then taken up in DCM and this solution was then added dropwise to rapidly stirring ether (100 mL).This usually gives a finely divided solid that could be filtered and dried. (Note: The cinchonine derivedPTCs are usually very insoluble. The quinidine derived PTCs are often completely soluble at the endof the reaction.) The di(t-butyl)benzyl PTC was prepared according to the standard procedure aboveand was filtered directly from the reaction mixture.

The synthetic route of 485-71-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Zhang, Tao; Scalabrino, Gaia; Frankish, Neil; Sheridan, Helen; Molecules; vol. 23; 7; (2018);,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

Brief introduction of 485-71-2

As the paragraph descriping shows that 485-71-2 is playing an increasingly important role.

485-71-2,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.485-71-2,Cinchonidine,as a common compound, the synthetic route is as follows.

Resolution of the enantiomers of 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4,5-dihydro-pyrazole-3-carboxylic acid The resolution of the enantiomers of 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4,5-dihydro-pyrazole-3-carboxylic acid was carried out via reaction with the following chiral bases: BrucineQuinine(-)-Cinchonidine(+)-CinchonineR-(+)-1-Phenylethylamine(1 R,2S)-(-)-Ephedrine hydrochloride(1S,2R)-(+)-Ephedrine hydrochloride. In each case the reactions were carried out with 0.5 and 1 equivalents of base in respect to 1 equivalent of the acid compound and by using the following solvents EthanolAcetoneAcetonitrilDioxaneEthylacetateChloroform. The results are summarized in the following tables. It may be understood that the afore mentioned crystallisation experiments that are not reflected in the following tables did not yield crystals of the respective salts under the given conditions. However, suitable conditions for crystallization of these salts can be determined by those skilled in the art via routine experiments. In the following tables Acid represents racemic 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4,5-dihydro-pyrazo)e-3-carboxylic acid R-Acid represents the respective derivative of (R)-5-( 4-chlorophenyl)-1-(2,4-dichlorophenyl)-4,5-dihydro-pyrazole-3-carboxylic acid S-Acid represents the respective derivative of (S)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4,5-dihydro-pyrazole-3-carboxylic acidProcesses for crystallisation: Process A: A solution of the chiral base was added on top of a solution of the racemic acid at room temperature.Process C: A solution of the racemic acid was added on top of a solution of the chiral base. The mixture was heated to reflux and solvent was added until dissolution was complete. The solution was left to crystallisation at r.t.Process D: The chiral base was directly added on top of a solution of the racemic acid at room temperature.Process E: The chiral base was directly added on top of a solution of the racemic acid at reflux temperature.Process F: The solution of the salt was evaporated to dryness. The residue was dissolved in a minimum amount of the solvent under reflux heating. The solution was left to crystallisation at r.t.Resolution with (-)-Cinchonidine [Show Image] Acid g (mmol) Eq. amine Proc. Solvent for crystallisation T CrystYield 1st Cryst. % % S-Acid % R-Acid0,4 g (1,09 mmol) 1 F 2ml dioxane r.t 31 94,4 5,60,4 g (1,09 mmol) 1 F 19ml Ethylacetate r.t 28,5 95,8 4,20,4 g (1,09 mmol) 1 F 20ml acetone r.t. 19,6 96,9 3,10,4 g (1,09 mmol) 1 F 24ml acetonitrile r.t 42 85,8 14,1

As the paragraph descriping shows that 485-71-2 is playing an increasingly important role.

Reference£º
Patent; Laboratorios del Dr. Esteve S.A.; EP1944293; (2008); A1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI