Category: 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,485-71-2

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

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

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

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 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

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.,485-71-2

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.

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

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

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 phase-transfer catalysts (C1-C11) were synthesized according to the proceduresbelow. To a solution of cinchonidine (1.00 g, 3.4 mmol) in THF (50 mL) was addedthe aryl benzyl bromides (3.4 mmol). The mixture was heated for 6-8 h at reflux.After cooling to room temperature, the mixture was poured into MTBE (150 mL)under stirring. The precipitated solid was filtrated and recrystallized fromCH3OH/MTBE to afford C1-C11

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

Reference£º
Article; Li, Ruipeng; Liu, Zhenren; Chen, Liang; Pan, Jing; Zhou, Weicheng; Beilstein Journal of Organic Chemistry; vol. 14; (2018); p. 1421 – 1427;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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

General procedure: (Part 1) To a stirred solution of Cinchona alkaloid (either Quinine, Quinidine, Cinchonine or Cinchonidine) (1 equiv.) in THF (0.1 M) was added the required arylmethyl halide compound (1.2 equiv.) at room temperature. The reaction mixture was refluxed overnight, cooled to room temperature and all volatiles were removed invacuo. The residue was then dissolved in CH2Cl2 (typically 2 mL for 1 mmol of starting material) and the resulting solution was added dropwise onto Et2O (typically 30 mL for 1 mmol of starting material) with vigorous stirring. The resulting precipitate was then filtered, washed thoroughly with Et2O, and further dried under high vacuum for 2 hours, yielding the intermediate alcohol product in an excellent yield. (Part2) This product (1 equiv.) was dissolved in CH2Cl2 (0.2 M). Methyl iodide (3 equiv.) and an aqueous sodium hydroxide solution (50 %w, 5 equiv.) were successively added at room temperature. The reaction mixturewas stirred at room temperature for 4 h, before water (typically 20 mL for 1 mmol of starting material) was added to quench the reaction. The organic layer was separated and the aqueous layer was extracted with CH2Cl2. The combined organic extracts were dried over Na2SO4, and concentrated in vacuo (N.B: washing with brine is prohibited to avoid the I/Cl anion exchange). Purification by column chromatography on silica gel, eluting with MeOH/Acetone/CH2Cl2 (0:10:90 to 10:10:90), afforded the desired Cinchona alkaloid quaternary ammonium salt in a moderate to excellent yield.

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

Reference£º
Article; Antien, Kevin; Viault, Guillaume; Pouysegu, Laurent; Peixoto, Philippe A.; Quideau, Stephane; Tetrahedron; vol. 73; 26; (2017); p. 3684 – 3690;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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

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

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 phase-transfer catalysts (C1-C11) were synthesized according to the proceduresbelow. To a solution of cinchonidine (1.00 g, 3.4 mmol) in THF (50 mL) was addedthe aryl benzyl bromides (3.4 mmol). The mixture was heated for 6-8 h at reflux.After cooling to room temperature, the mixture was poured into MTBE (150 mL)under stirring. The precipitated solid was filtrated and recrystallized fromCH3OH/MTBE to afford C1-C11

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

Reference£º
Article; Li, Ruipeng; Liu, Zhenren; Chen, Liang; Pan, Jing; Zhou, Weicheng; Beilstein Journal of Organic Chemistry; vol. 14; (2018); p. 1421 – 1427;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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 phase-transfer catalysts (C1-C11) were synthesized according to the proceduresbelow. To a solution of cinchonidine (1.00 g, 3.4 mmol) in THF (50 mL) was addedthe aryl benzyl bromides (3.4 mmol). The mixture was heated for 6-8 h at reflux.After cooling to room temperature, the mixture was poured into MTBE (150 mL)under stirring. The precipitated solid was filtrated and recrystallized fromCH3OH/MTBE to afford C1-C11

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

Reference£º
Article; Li, Ruipeng; Liu, Zhenren; Chen, Liang; Pan, Jing; Zhou, Weicheng; Beilstein Journal of Organic Chemistry; vol. 14; (2018); p. 1421 – 1427;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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

4-Hydroxyphenylacetic acid(40 mg, 0.263 mmol) and cinchonidine (77.4 mg, 0.263 mmol) were both dissolved in ethyl methyl ketone. Crystals were obtained afterone week.

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

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

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 (-)-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, 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