September 18, 2020 | Chiral oxygen ligands

A new synthetic route of 4254-15-3

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,4254-15-3,(S)-Propane-1,2-diol,its application will become more common.

A common heterocyclic compound, 4254-15-3,(S)-Propane-1,2-diol, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route. 4254-15-3

(S)-(+)-1,2-propanediol (2.506 g, 32.9 mmol) and 4-methylbenzene-1-sulfonyl chloride (6.91 g, 36.2 mmol) in dichloromethane (DCM) (80 mL) Medium solution,Triethylamine (6.89 mL, 49.4 mmol),Subsequently 4-dimethylaminopyridine (0.201 g, 1.647 mmol) was added.The reaction was stirred at room temperature for 16 hours.The reaction was quenched with saturated aqueous ammonium chloride (20 mL) and the layers were separated.Extract the aqueous portion with DCM (2 ¡Á 20 mL),The combined organic layers were washed with saturated aqueous sodium bicarbonate (20 mL) and brine (20 mL).The organic portion is dried over MgSO4, filtered,Concentrate under reduced pressure to give a residue that isPurification by silica gel chromatography eluting with 10-100% ethyl acetate: heptane gave the product (4.56 g, 60% yield).

Reference£º
Patent; Abbvie Incorporated; Argiriadi, Maria A.; Breinlinger, Eric C.; Chien, Ellen Yulin Tsai; Cowart, Marlon D.; Frank, Kristine E.; Friedman, Michael M.; Hardy, David J.; Herold, J. Martin; Liu, Huaqing; Chu, Wei; Scanio, Marc J.; Schrimpf, Michael R.; Vargo, Thomas R.; Van Epps, Stacy A.; Webster, Matthew P.; Little, Andrew J.; Dunstan, Teresa A.; Katcher, Matthew H.; Schedler, David A.; (232 pag.)JP6557436; (2019); B1;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

A new synthetic route of 24621-61-2

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,24621-61-2,(S)-Butane-1,3-diol,its application will become more common.

A common heterocyclic compound, 24621-61-2,(S)-Butane-1,3-diol, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route. 24621-61-2

Triethylamine (1.173 g) is added dropwise to a solution of 2.246 g triisopropylchlorosilane and 1 g (S)-(+)-1,3-butanediol in 15 ml of dry tetrahydrofuran. The mixture is stirred for 48 hours at room temperature, then is diluted with 400 ml of tert-butyl methyl ether and washed respectively with 30 ml 1N HCl, 50 ml water and 50 ml of brine. The organic phase is dried (sodium sulphate), filtered and evaporated to dryness. The residue is purified by means of flash column chromatography (SiO2 60F) to provide the title compound as a colorless oil. Rf=0.31 (EtOAc-heptane 1:5).

Reference£º
Patent; Herold, Peter; Mah, Robert; Stutz, Stefan; Tschinke, Vincenzo; Schumacher, Christoph; Stojanovic, Aleksandar; Jotterand, Nathalie; Behnke, Dirk; US2007/167433; (2007); A1;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

Some scientific research about (2S,3S)-Butane-2,3-diol

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,19132-06-0,(2S,3S)-Butane-2,3-diol,its application will become more common.

19132-06-0 A common heterocyclic compound, 19132-06-0,(2S,3S)-Butane-2,3-diol, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

To a 500-mL, 3-necked-RBF (equipped with a H20-cooled reflux condenser and an HCl trap) was added (2s,3s)-(+)-2,3-butanediol (Aldrich; 15.00 mL, 166 mmol) and CC14 (120 mL). SOCl2, reagentplus (14.57 mL, 200 mmol) was then added drop wise via a syringe over a period of 20 min and the resulting mixture was heated to 98C for 45 min, then allowed to cool to rt. The reaction mixture was then cooled in an ice/H20 bath, MeCN (120 mL) and H20 (150 mL) were added followed by ruthenium(III) chloride (0.035 g, 0.166 mmol). Sodium periodate (53.4 g, 250 mmol) was then added slowly portion wise over 30 min. The resulting biphasic brown mixture was stirred vigorously while allowed to reach rt for a period of 1.5 h (internal temperature never increased above rt). TLC (50% EtOAc in heptanes) showed complete conversion. The crude mixture was then poured into ice H20 and extracted twice with 300 mL of Et20. The combined organic layers were washed once with 200 mL of sat. sodium bicarbonate, washed once with 200 mL of brine, dried over Na2S04; and concentrated by rotary evaporation to give (4S,5S)-4,5-dimethyl-l,3,2- dioxathiolane 2,2-dioxide (21.2 g, 139 mmol) as a red oil.

Reference£º
Patent; AMGEN INC.; BROWN, Sean P.; LI, Yunxiao; LIZARZABURU, Mike Elias; LUCAS, Brian S.; PARAS, Nick A.; TAYGERLY, Joshua; VIMOLRATANA, Marc; WANG, Xianghong; YU, Ming; ZANCANELLA, Manuel; ZHU, Liusheng; GONZALEZ BUENROSTRO, Ana; LI, Zhihong; (279 pag.)WO2016/33486; (2016); A1;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

The origin of a common compound about 538-58-9

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,538-58-9,1,5-Diphenylpenta-1,4-dien-3-one,its application will become more common.

A common heterocyclic compound, 538-58-9,1,5-Diphenylpenta-1,4-dien-3-one, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route. 538-58-9

538-58-9, General procedure: 9-Amino(9-deoxy)-epi-quinine (6.5 mg, 0.02 mmol), divinyl ketone 1 (0.1 mmol), nitromethane (262 muL, 3.0 mmol), Proton-sponge (4.3 mg, 0.02 mmol) and benzoic acid (4.9 mg, 0.04 mmol) were dissolved in chlorobenzene (238muL). After stirred at 40 oC for 144 h, the reaction mixture was purified by flash chromatography on silica gel (EtOAc/petroleum ether).

Reference£º
Article; Yao, Yongqi; Liu, Yingying; Ye, Ling; Chen, Feng; Li, Xinying; Zhao, Zhigang; Li, Xuefeng; Tetrahedron; vol. 73; 16; (2017); p. 2311 – 2315;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

Some scientific research about 24621-61-2

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,(S)-Butane-1,3-diol,24621-61-2,its application will become more common.

To a solution of (S)+}1,3-butanediol (10.0 g, 0.110 mol), was added triphenylmethylchloride (33.0 g, 0.330 mol), 4-dimethylaminopyridine (1.40 g, 11.5 mmol) in CH2Cl/pyridine (1:1, 500 mL).Stirring was continued over 48 h. The solvent was removed, the mixture was diluted with ether, washed with brine and dried over Na2SO4. The organic solution was filtered and concentrated. Silica gel chromatography with (5% ethyl acetate/hexanes) produced a clear oil (24 g) in 70% yield., 24621-61-2

Reference£º
Patent; Bristol-Myers Squibb Company; Merck & Co. Inc.; US6967196; (2005); B1;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

New downstream synthetic route of 24621-61-2

Representative example 44: Synthesis of 1-((R)-3-(2-(4-hydroxy-1-((2R,3S)-2- propyl-1-(3-(trifluoromethyl)picolinoyl)-3-(5-(trifluoromethyl)thiophen-3- yloxy)piperidine-3-carbonyl)piperidin-4-yl)phenoxy)butyl)cyclobutanecarboxylic acid A31. Step 1: To a 0C DCM (100 mL) solution of (S)-(+)-1 ,3-Butanol (7g, 77.6 mmol) containing Et^N (14 mL, 1.3equiv) was added drop wise a DCM solution (60 mL) of TsCI (1.05 equiv, 15g). Reaction was warmed-up to Rt and stirred overnight. After 18 hours, the DCM layer was washed with HCI 1.0N (X2), then NaHC03, then brine. Organic layer was dried over MgS04, filtered and concentrated down to 15 g of crude oil. The residue was purified by silica gel chromatography (10% to 40% EtOAc in hexanes) to provide 13 g (69% yield) of (S)-3-hydroxybutyl 4- methylbenzenesulfonate 94.

Reference£º
Patent; SCHERING CORPORATION; BOGEN, Stephane, L.; MA, Yao; WANG, Yaolin; LAHUE, Brian Robert; NAIR, Latha, G.; SHIZUKA, Manami; VOSS, Matthew Ernst; KIROVA-SNOVER, Margarita; PAN, Weidong; TIAN, Yuan; KULKARNI, Bheemashankar, A.; GIBEAU, Craig, R.; LIU, Yuan; SCAPIN, Giovanna; RINDGEN, Diane; DOLL, Ronald, J.; GUZI, Timothy, J.; HICKLIN, Danny, J.; NOMEIR, Amin; SEIDEL-DUGAN, Cynthia; SHIPPS, Gerald, W., Jr.; MACCOSS, Malcolm; WO2011/46771; (2011); A1;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

A new synthetic route of (S)-Butane-1,3-diol

Example 25 (4-{(R)-3-[(2-CHLORO-3-TRIFLUOROMETHYL-BENZYL)-2, 2-DIPHENYLETHYL-AMINO]-BUTOXY}-INDOL-1- YL) acetic acid hydrochloride salt a) Toluene-4-sulfonic acid (S)-3-hydroxy-butyl ester To a solution of (S)-1, 3-butanediol (2.0 g, 22.0 MMOL) and Et3N (4.6 mL, 33.0 MMOL) in CH2CI2 (20 mL) at-20 C was added p-toluenesulfonyl chloride (4.46 g, 23.0 MMOL) and the reaction mixture was then warmed to RT and stirred overnight. The reaction mixture was washed with H20 and brine, dried over NA2SO4, filtered, and concentrated to give the title compound as a yellow oil (5.2 G, 96%)a) Toluene-4-sulfonic acid (S)-3-hydroxy-butyl ester To a solution of (S)-1, 3-butanediol (2.0 G, 22.0 MMOL) and Et3N (4.6 mL, 33.0 MMOL) in CH2CI2 (20 mL) at-20 C was added p-toluenesulfonyl chloride (4.46 g, 23.0 MMOL) and the reaction mixture was then warmed to RT and stirred overnight. The reaction mixture was washed with H20 and brine, dried over NA2SO4, filtered, and concentrated to give the title compound as a yellow oil (5.2 G, 96%), 24621-61-2

Reference£º
Patent; SMITHKLINE BEECHAM CORPORATION; WO2005/23196; (2005); A2;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

A new synthetic route of 1,5-Diphenylpenta-1,4-dien-3-one

General procedure: 9-Amino(9-deoxy)-epi-quinine (6.5 mg, 0.02 mmol), divinyl ketone 1 (0.1 mmol), nitromethane (262 muL, 3.0 mmol), Proton-sponge (4.3 mg, 0.02 mmol) and benzoic acid (4.9 mg, 0.04 mmol) were dissolved in chlorobenzene (238muL). After stirred at 40 oC for 144 h, the reaction mixture was purified by flash chromatography on silica gel (EtOAc/petroleum ether).

The origin of a common compound about 24621-61-2

(S)-(+)-Butane-1 ,3-diol (3.00 mmol, 0.270 g) was added to a stirred solution of imidazole (5.99 mmol, 0.41 g) and tert-butyldimethylsilyl chloride (3.00 mmol, 0.45 g) at room temperature. After six hours at room temperature water (50 mL) was added and extracted twice with dichloromethane (20 mL). The combined organic extracts were washed with brine, dried (sodium sulfate) and concentrated in vacuo to yield (S)-4- (tert-butyldimethylsilyloxy)butan-2-ol (0.654 g).

Reference£º
Patent; N.V. ORGANON; MAN de,, Adrianus Petrus Antonius; REWINKEL,, Johannes Bernardus Maria; JANS,, Christiaan Gerardus Johannes Maria; RAAIJMAKERS,, Hans Cornelis Andreas; WIJKMANS,, Jacobus Cornelis Henricus Maria; WO2011/95556; (2011); A1;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

A new synthetic route of 1,5-Diphenylpenta-1,4-dien-3-one

General procedure: In a general procedure, dibenzylidene acetone (1 mmol), N,N-dimethylbarbituric acid/barbituric acid/thiobarbituric acid(1 mmol) and 4 mL of ethanol:water (1:1) were taken in a 50 mL round-bottomed flask. 10 mol% of tetrabutyl ammonium bromide (TBAB) was added to the mixture, and the contents were stirred. The reaction mixture was refluxed and the progress of the reaction was monitored by TLC using ethyl acetate:petroleum ether (30:70) as eluent for disappearance of active methylene compounds. After completion of the reaction, the reaction mixture was allowed to cool to room temperature and diluted with water (5 mL). The solid obtained was filtered at pump and washed with water:ethanol (2:1). The product was recrystallized with ethanol. The products were characterized by their spectral data.

Reference£º
Article; Aggarwal, Komal; Khurana, Jitender M.; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; vol. 143; (2015); p. 288 – 297;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate