Day: August 14, 2020

4254-15-3, (S)-Propane-1,2-diol is a chiral-oxygen-ligands compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

(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).

As the paragraph descriping shows that 4254-15-3 is playing an increasingly important role.

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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.24621-61-2,(S)-Butane-1,3-diol,as a common compound, the synthetic route is as follows.

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%)

The synthetic route of 24621-61-2 has been constantly updated, and we look forward to future research findings.

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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.538-58-9,1,5-Diphenylpenta-1,4-dien-3-one,as a common compound, the synthetic route is as follows.

General procedure: A mixture of unsaturated ketone 1a (60.7 mg, 0.25 mmol) and phosphonium salt 2a (198.6 mg, 0.45 mmol) in CH3CN (2 mL) was stirred for 5 min. Then DBU (127 muL) in CH3CN (0.5 mL) was added. The reaction mixture was stirred at 60 C for 6 h and then air was introduced with a balloon for another 42 h. After the reaction was completed, the reaction mixture was filtered through a short silica gel column and washed with DCM. The filtrate was concentrated under reduced pressure and the residue was purified by flash chromatography (PE/EtOAc, 60/1) to afford 3a as a colorless oil (69.3 mg, 86% yield).

As the paragraph descriping shows that 538-58-9 is playing an increasingly important role.

Reference£º
Article; Shu, Zhen-Cao; Zhu, Jian-Bo; Liao, Saihu; Sun, Xiu-Li; Tang, Yong; Tetrahedron; vol. 69; 1; (2013); p. 284 – 292;,
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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.24621-61-2,(S)-Butane-1,3-diol,as a common compound, the synthetic route is as follows.

Example 1; Preparation of (3S)-1-p-Toluenesulfonyloxy-3-triethylsilyloxy-butane (2); To a stirred solution of the (S)-(+)-1,3-butanediol 1 (1 g, 11.1 mmol), DMAP (30 mg, 0.25 mmol) and Et3N (4.6 mL, 3.33 g, 33 mmol) in anhydrous methylene chloride (20 mL) p-toluenesulfonyl chloride (2.54 g, 13.3 mmol) was added at 0 C. The reaction mixture was stirred at 4 C. for 22 h. Methylene chloride was added and the mixture was washed with water, dried (Na2SO4) and concentrated under reduced pressure. A residue was chromatographed on silica gel with hexane/ethyl acetate (8:2, then 1:1) to afford the tosylate (2.31 g, 85% yield) as a colorless oil.

24621-61-2 (S)-Butane-1,3-diol 446973, achiral-oxygen-ligands compound, is more and more widely used in various.

Reference£º
Patent; DeLuca, Hector F.; Clagett-Dame, Margaret; Plum, Lori A.; Chiellini, Grazia; Grzywacz, Pawel; US2008/81800; (2008); 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

4254-15-3, (S)-Propane-1,2-diol is a chiral-oxygen-ligands compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

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.

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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

24621-61-2, (S)-Butane-1,3-diol is a chiral-oxygen-ligands compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

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 H20 (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.

As the paragraph descriping shows that 24621-61-2 is playing an increasingly important role.

Reference£º
Patent; SMITHKLINE BEECHAM CORPORATION; WO2004/43939; (2004); 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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.4254-15-3,(S)-Propane-1,2-diol,as a common compound, the synthetic route is as follows.

The four (4) step reaction sequence starting from 103-1 and 103-2 (prepared as shown from S-(+)-1,2-propanediol (103-0)) provided Boc-T103a in a very good overall yield of 85%. The alternatively protected analogue Ddz-T103a was prepared using the same procedure with an overall yield of 55% [1.4 g Ddz(2RMe)opy18 was obtained starting from 1 g (5.8 mmol) of 103-1]. Synthesis of the Boc-T103b stereoisomer proceeds similarly, but starting from R-(-)-1,2-propanediol.TLC: Rf: 0.3 (100% EtOAc)

The synthetic route of 4254-15-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Tranzyme Pharma Inc.; US2008/194672; (2008); 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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.4254-15-3,(S)-Propane-1,2-diol,as a common compound, the synthetic route is as follows.

Example 33 : (2R, 75R)-2-[(l-Aminoisoquinolin-6-yl)amino]-8-fluoro-7- {[(25)-l- hydroxypropan-2-yl]oxy } -4, 15,20-trimethyl- 13 -oxa-4, 1 1- diazatricyclo[14.2.2.16, 10]henicosa-l(18),6,8, 10(21), 16, 19-hexaene-3, 12-dione; trifluoroacetic acid [00356] To a solution of (s)-(+)-l,2-propanediol (2.0 g, 26.3 mmol) in DMF (5 mL) was added TBS-C1 (5.94 g, 39.4 mmol) and imidazole (2.147 g, 31.5 mmol). The reaction was stirred at 25 ¡ãC for 18 h. The reaction mixture was partitioned between ethyl acetate and sat. ammonium chloride. The organic phase was washed with sat. ammonium chloride and brine, dried (MgS04) and concentrated in vacuo. The crude product was purified by flash chromatography to give 33A (4.0 g, 80percent yield) as a colorless oil. 33B: (5)-Benzyl 2-((l-((tert-butyldimethylsilyl)oxy)propan-2-yl)oxy)-3-fluoro-5- nitrobenzyl(methyl)carbamate [00357] To a solution of 27B (400 mg, 1.197 mmol), 33A (251 mg, 1.316 mmol) and triphenylphosphine (345 mg, 1.316 mmol) in THF (10 mL) at 0 ¡ãC, was added DIAD (0.256 mL, 1.316 mmol) dropwise. The reaction mixture was allowed to slowly warm to rt and stirred for 16 h, then was concentrated. The crude product was purified by flash chromatography (0 to 40percent ethyl acetate/hexanes) to give 33B (577 mg, 1.139 mmol, 95percent yield) as colorless oil. MS (ESI) m/z: 507.1 [M+1]+. H MR (400 MHz, chloroform-d) delta ppm 7.78 – 7.94 (2 H, m) 7.27 – 7.43 (5 H, m) 5.17 (2 H, d, J=20.1 Hz) 4.46 – 4.74 (3 H, m) 3.65 – 3.81 (2 H, m) 2.97 (3 H, d, J=15.8 Hz) 1.31 (3 H, t, J=7.0 Hz) 0.81 (9 H, d, J=7.0 Hz) -0.05 – 0.04 (6 H, m) rotamers. 33C: (S)-4-((l-((tert-Butyldimethylsilyl)oxy)propan-2-yl)oxy)-3-fluoro-5- ((methylamino)methyl)aniline [00358] To a degassed solution of 33B (573 mg, 1.131 mmol) in MeOH (10 mL), was added 10percent Pd-C (50 mg, 0.047 mmol). The mixture was evacuated and flushed with H2 (3X), then was stirred under an atmosphere of H2 for 8 h. The mixture was filtered and concentrated to give 33C (382 mg, 1.115 mmol, 99percent yield) as a pale brown oil. MS (ESI) m/z: 343.1 [M+l]+. PI MR (400 MHz, chloroform-d) delta ppm 6.40 (1 H, d, J=1.8 Hz) 6.33 (1 H, dd, J=12.5, 2.8 Hz) 4.20 (1 H, sxt, J=5.7 Hz) 3.62 – 3.79 (4 H, m) 3.53 (2 H, br. s.) 2.40 (3 H, s) 1.25 (3 H, d, J=6.3 Hz) 0.89 (9 H, s) 0.05 (6 H, s). 33D: tert-Butyl N- {6-[({[(5-amino-2- { [(25)- l-[(tert-butyldimethylsilyl)oxy]propan-2- yl]oxy } -3 -fluorophenyl)methyl](methyl)carbamoyl} ( {4-[(2R)- 1 -hydroxypropan-2-yl]-3 – methylphenyl} )methyl)amino]isoquinolin- 1 -yl} -N-[(tert-butoxy)carbonyl]carbamate [00359] To Intermediate 5 (100 mg, 0.515 mmol), Intermediate 1 (185 mg, 0.515 mmol), and glyoxylic acid monohydrate (47.4 mg, 0.515 mmol), were added DMF (6.00 mL) and acetonitrile (6 mL). The mixture was stirred at 80 ¡ãC for 1 h, then was cooled to rt. To the mixture were added sequentially 33C (201 mg, 0.587 mmol), DMF (6.00 mL), TEA (0.215 mL, 1.546 mmol) and BOP (251 mg, 0.567 mmol). The reaction mixture was stirred at rt for 1 h, then was diluted with H20 and extracted with EtOAc (3X). The extract was washed with brine, dried ( a2S04) and concentrated. The crude product was purified by flash chromatography (1 to 15percent MeOH/methylene chloride) to give 33D (422 mg, 0.474 mmol, 92percent yield) as an orange foam. MS (ESI) m/z: 890.3 [M+l]+. H MR: complicated due to presence of diastereomers and amide rotamers. Example 33 [00360] To a solution of 33D (417 mg, 0.468 mmol) in dichloromethane (10 mL) and acetonitrile (5 mL) at 0 ¡ãC, was added phosgene (20percent in toluene, 0.243 mL, 0.492 mmol) dropwise. The mixture was stirred at 0 ¡ãC for 20 min, then was removed from the cooling bath and bubbled with Ar for 20 min. This mixture was added dropwise via a syringe pump into a solution of TEA (0.392 mL, 2.81 mmol) in dichloromethane (190 mL) over 5 h. The reaction mixture was allowed to stir at rt for 11 h, and then concentrated. The crude product was purified by flash chromatography (1 to 15percent MeOH/methylene chloride) to give a mixture of diastereoisomers. The diastereomers were separated by a prep chiral HPLC (R,R-Whelk-0 column 21.1 x 250 mm). The desired fractions were combined and concentrated. The residue was treated with TFA (4 mL) for 15 min. The reaction mixture was concentrated and purified by prep HPLC to give Example 33 (52.9 mg, 0.074 mmol, 31.4percent yield) white solid. MS (ESI) m/z: 602.2 [M+l]+. NMR (400 MHz, methanol-d4) delta ppm 8.05 (1 H, d, J=9.3 Hz) 7.64 (1 H, dd, J=7.8, 1.8 Hz) 7.44 (1 H, d, J=7.8 Hz) 7.31 (1 H, d, J=7.0 Hz) 7.18 – 7.23 (2 H, m) 6.91 (1 H, d, J=7.3 Hz) 6.83 (1 H, d, J=2.3 Hz) 6.53 (1 H, dd, J=12.4, 2.4 Hz) 5.73 (1 H, s) 5.66 (1 H, br. s.) 5.37 (1 H, d, J=17.1 Hz) 4.65 (1 H, t, J=11.0 Hz) 4.27 – 4.38 (1 H, m, J=5.7, 5.7, 5.7, 5.7, 5.4 Hz) 4.06 (1 H, d, J=17.3 Hz) 3.96 (1 H, dd, J=10.8, 4.3 Hz) 3.63 (2 H, d, J=4.8 Hz) 3.43 – 3.55 (1 H, m) 3.27 (3 H, s) 2.34 (3 H, s) 1.30 (3 H, d, J=7.0 Hz) 1.27 (3 H, d, J=6.3 Hz). Analytical HPLC (low pH, 254 nM): Sunfir…

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Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; ZHANG, Xiaojun; GLUNZ, Peter W.; PRIESTLEY, Eldon Scott; JOHNSON, James, A.; WURTZ, Nicholas, Ronald; LADZIATA, Vladimir; WO2013/184734; (2013); 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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.4254-15-3,(S)-Propane-1,2-diol,as a common compound, the synthetic route is as follows.

General procedure: A 45percent solution of hydrogen bromide in acetic acid (33.0 g, 23.2 mL) was added dropwise over 10 min to 60.3 mmol optically active diol 4a-f with stirring and ice-cooling. The solution was stirred at 0 ¡ãC for 5 min, and next at room temperature for 45 min. Next, water (100 mL) was added, and the mixture was alkalized to pH 8 with solid Na2CO3. The solution was immediately extracted with ethyl ether (5 .x. 60 mL), and the combined extracts were dried over anhydrous Na2SO4. The ether was evaporated, and the product was distilled under reduced pressure or purified by silica gel column chromatography with gradient AcOEt-hexane 9:1.

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Reference£º
Article; Poterala, Marcin; Plenkiewicz, Jan; Tetrahedron Asymmetry; vol. 22; 3; (2011); p. 294 – 299;,
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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.24621-61-2,(S)-Butane-1,3-diol,as a common compound, the synthetic route is as follows.

EXAMPLE 38 2-((3S)-3-Hydroxy- 1-butyloxy)-3-(4-methylsulfonyl)phenyl-5-trifluoromethylpyridine To a solution of (S)-1,3-butanediol (807 mg) in DMF (10 mL) at 0 C. was added potassium t-butoxide (7.2 mL of a 1M solution in THF). After 1 h, the mixture was cooled to -20 C. and then 2-chloro-3-(4-methylsulfonyl)phenyl-5-trifluoromethylpyridine (1 g) was added as a solid. The resulting mixture was stirred for 24 h, warming to r.t. To the mixture was added saturated NH4Cl and the mixture was extracted with ethyl acetate. The organics were dried (MgSO4) and concentrated. Flash chromatography (1:1 hexane/ethyl acetate) provided the title compound as a white solid (323 mg). 1 H NMR (300 MHz, acetone-d6): d 1.15 (d, 3H), 1.75-2.00 (m, 2H), 3.15 (s, 3H), 3.65 (d, 1H), 3.85-4.00 (m, 1H), 4.60 (dd, 2H), 7.95 (d, 2H), 8.03 (d, 8.10 (d, 1H), 8.57 (d, 1H).

24621-61-2 (S)-Butane-1,3-diol 446973, achiral-oxygen-ligands compound, is more and more widely used in various.

Reference£º
Patent; Merck Frosst Canada & Co.; US6046217; (2000); A;,
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