M.W:0-100 | Page 276 of 277 | Chiral oxygen ligands

A new synthetic route of (S)-Propane-1,2-diol

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

Under an atmosphere of argon, trifluoromethanesulfonic acid (485 muEpsilon; 822 mg; 5.47 mmol; 5.0 eq) was added dropwise at 0-5¡ãC (ice/brine bath) to a solution of l-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-(5- fluoroimidazol-l-yl)ethanone (400 mg ; 1.09 mmol) and (2S)-propane-l,2-diol (3.33 g; 43.8 mmol; 40.0 eq) in anhydrous toluene (3.0 mL). The resulting mixture was allowed to warm up to room temperature, then refluxed for 20h. Thereafter the reaction mixture was allowed to cool down to room temperature, diluted with ethyl acetate, washed with saturated aqueous sodium bicarbonate, the combined organic layers were – – dried (MgSO i) and concentrated to dryness in vacuo. The residue was purified by chromatography over silica gel, eluted with a mixture of dichloromethane/methanol (100:0 to 90: 10). Evaporation of the solvents in vacuo afforded 271 mg (54percent) of l-[[2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-l,3-dioxolan-2- yl]methyl]-5-fluoro-imidazole (approx. 59:41 mixture of diastereoisomers) as a colourless solid. MS (ESI): 423.1 ([M+H]+)

Reference£º
Patent; BAYER CROPSCIENCE AKTIENGESELLSCHAFT; BAYER AKTIENGESELLSCHAFT; COQUERON, Pierre-Yves; BERNIER, David; GENIX, Pierre; MILLER, Ricarda; NAUD, Sebastien; WITTROCK, Sven; BRUNET, Stephane; KENNEL, Philippe; MEISSNER, Ruth; WACHENDORFF-NEUMANN, Ulrike; GOeRTZ, Andreas; (104 pag.)WO2018/60088; (2018); 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

New downstream 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,(S)-Propane-1,2-diol,4254-15-3,its application will become more common.

(S)-Methylethylene Bis(methylsulfonate), CAS 270577-16-7, Compound A Scheme 1,was prepared from (S)-(+)-1,2-propanediol (CAS 4254-15-3, Sigma Aldrich Chemical Company) and methane sulfonyl chloride (CAS 124-63-O, Sigma Aldrich Chemical Company) according to the procedure of T. Harada, T. Mai, T. Tuyet, and A. Oku, Organic Letters (2000), 2(9), 1319-1322.

Reference£º
Patent; Kent State University; Kent Displays Incorporated; US2012/273725; (2012); 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 4254-15-3

Compound M31:; To a solution of (S)-1 ,2-propandiol (5 mmol) in 5 ml_ of anhydrous CH2CI2 were added 2-methyl-1-butene (5.5 mmol) and BF3 etherate (0.5 mmol) at room temperature. The stirring was continued for another 24 h. The solvent was removed by vacuum, and the residue was purified by chromatograph on silica gel to afford intermediate (4 mmol, 80 percent yield) as oil. Then, to a suspension of this intermediate and imidazole (6 mmol) in 6 ml_ of anhydrous THF was added 4.8 mL of TBDMSCI (1 M in THF) at 0 0C. The solvent was removed by vacuum, and the residue was re-dissolved in Et2O. The heterogeneous mixture was filtered over a pad of Celite. The filtrate was washed with 1N HCI, water and brine, dried over Na2SO4 and concentrated in vacuo. The residue was chromatographed to give pure M31 (0.34 mmol, 85percent yield) as oil.

Reference£º
Patent; UNIVERSITY OF CONNECTICUT; WO2006/44381; (2006); 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

The origin of a common compound about 4254-15-3

Step 1 To (S)-propane diol (4.89 g, 64.2 mmol) in DCM (20 ml_) at-20 C (CO2/ ethylene glycol bath) was added TEA (11.2 mL, 80.3 mmol) followed by p-toluenesulfonyl chloride (12.3 g, 64.3 mmol) in DCM (26 mL) dropwise over 30 minutes. Allowed the cold bath to expire while stirring for 26 h. Added DCM and washed the reaction with 1 N HCI, water, and brine. Dried (MgSO4) the organic layer, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (0-40% EtOAc/Hex over 40 minutes) to provide the tosylate (8.37 g, 36 .4 mmol).

Reference£º
Patent; SCHERING CORPORATION; WO2009/5646; (2009); 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

The origin of a common compound about (S)-Butane-1,3-diol

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,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

e) (S)-4-Triisopropylsilanvloxv-butan-2-olTriethylamine (1.173 g) is added dropwise to a solution of 2.246 g triisopropylchlorosilaneand 1 g (S)-(+)-1,3-butanediol in 15 ml of dry tetrahydrofuran. The mixture is stirred for 48hours at room temperature, then is diluted with 400 ml of tert-butyl methyl ether and washedrespectively with 30 mM N HCI, 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 offlash column chromatography (SiO2 60F) to provide the title compound as a colorless oil.Rf = 0.31 (EtOAc- heptane 1:5).

Reference£º
Patent; SPEEDEL EXPERIMENTA AG; WO2006/5741; (2006); 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

New downstream synthetic route of 4254-15-3

Some scientific research about (S)-Butane-1,3-diol

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

24621-61-2 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.

Step E (2-TOLUENE-4-SULFONIC acid 3-hydroxy-butyl ester; A solution of (S)- (+)-1, 3-butanediol (9.5 g, 0.105 mol) and Et3N (12.8 g, 0.126 mol) in CH2C12 (200 mL) is treated with dibutyltin oxide (0.52 g, 2.08 mmol) and THENP-TOLUENESULFONYL chloride (20.09 g, 0.105 mol) is added as a solid in portions over 30 minutes at rt. The resultant mixture is stirred at rt for 17 hours under N2. The reaction is quenched with 1 N HC1 (50 mL), diluted with water and extracted with EtOAc. The organic layer is dried (NA2SO4), and the solvent is removed in vacuo to afford crude product that is absorbed on silica gel and purified by flash chromatography using 98/2 CH2C12/ACN (to elute the unreactedp-toluenesulfonyl chloride) and then 2/1 hexanes/acetone to afford 18. 67 g (73%) the title compound. Rf== 0.23, Rf bis-tosylate = 0.53 (98/2 CH2C12/ACN).

Reference£º
Patent; ELI LILLY AND COMPANY; WO2005/19151; (2005); 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 24621-61-2

Example 4 : (R)-2-(3-{3-[[2-Chloro-3-(trifluoromethyl) benzyl] (2,2- diphenylethyl) amino]-1-methyl-propoxy}-phenyl) acetic acid methyl ester ; a) Toluene-4-sulfonic acid- (S)-3-hydroxy-butyl ester; To a stirring solution of (S)-1, 3-butanediol (1.0 g, 0.01 mmol) and triethylamine (1.39 g, 0.014 mmol) in dichloromethane (10 mL) at-20C was added dropwise p-toluenesulfonyl chloride and the mixture was stirred for 2 h. The reaction mixture was then warmed to RT and stirred overnight. The reaction mixture was poured into cold H2O (20 mL), and extracted three times with dichloromethane. The organic extracts were then washed with brine. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to give 2.6 g (96% yield) of title compound as an oil. MS (ESI) 244.8 (M+). The crude tosylat was used without further purification.

Reference£º
Patent; SMITHKLINE BEECHAM CORPORATION; WO2003/82802; (2003); 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

General procedure: (R)-Ethyl 3-hydroxybutyrate (2.1 g, 16 mmol) and (R)-1,3 butanediol(1.0 g, 11 mmol) were combined and incubated with CAL-B (0.2 g,400 U) at 80 torr without solvent in a rotary evaporator. The reaction was monitored by withdrawing 5 muL portions of the reaction mixture,which were dissolved in 1.0 mL methanol for analysis by GC-MS. Upon consumption of the diol, the reaction mixture was taken up in dichloromethane,the beads were filtered and washed, and the solventremoved by rotary evaporation. Excess (R)-ethyl 3-hydroxybutyratewas removed by heating to 60 deg C under reduced pressure (1 torr).The residue was suspended in ethyl acetate, treated with activated carbon and filtered to yield (R)-3-hydroxybutyryl-(R)-3-hydroxybutyrateas a clear oil (1.2 g, 62%).

Reference£º
Article; Budin, Noah; Higgins, Erin; DiBernardo, Anthony; Raab, Cassidy; Li, Chun; Ulrich, Scott; Bioorganic Chemistry; vol. 80; (2018); p. 560 – 564;,
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 24621-61-2

Example 7A (2S)-4-((tert-butyl(dimethyl)silyl)oxy)-2-butanol A 0 C. solution of (S)-(+)-1,3-butanediol (2.1 g, 23.3 mmol), imidazole (1.74 g, 25.6 mmol), and N,N-dimethylformamide (1.0 mL) in dichloromethane (40 mL) was treated with tert-butyl-dimethylsilyl chloride (3.68 g, 23.3 mmol). The reaction mixture was warmed to room temperature, stirred overnight, quenched with saturated aqueous ammonium chloride and extracted with dichloromethane. The combined dichloromethane layers were dried (MgSO4), filtered and concentrated to afford of the desired product of sufficient purity for subsequent use without further purification in near quantitative yield. MS (DCI/NH3) m/z 205 (M+H)+; 1H NMR (300 MHz, CDCl3) delta3.95 (m, 1H), 3.79 (m, 2H), 3.27 (br s, 1H), 1.56 (m 2H), 1.11 (d, 3H), 0.82 (s, 9H), 0.016 (s, 6H).

Reference£º
Patent; Bennani, Youssef L.; Black, Lawrence A.; Dwight, Wesley J.; Faghih, Ramin; Gentles, Robert G.; Liu, Huaqing; Phelan, Kathleen M.; Vasudevan, Anil; Zhang, Henry Q.; US2001/49367; (2001); 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