Tag: M.W:0-100

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

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.

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.

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 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

To a solution of commercial available (s)-3-hydroxy butanol (10 g, Aldrich) in 50 mL of DMF, TsOH (20 mg, catalytic) and MeOPhCH (OMe) 2 (24 g) were added. After 3h at 35 C on a rotovap with slight vacuum, it was cooled and quenched with aq. Sat. NaHC03. The mixture was extracted with EtOAc (3x). The organic layers were washed with brine (2x), dried and concentrated. The crude product was evaporated with toluene (3x). [0230] The crude product was dissolved in 700 mL of CH2CI2. At 0 C, DIBAL-H solution (200 mL, 1.0 M, excess) was added. The reaction was warmed to room temperature overnight. Then it was quenched with methanol (50 mL), sat. Na2S04 at 0 C. The mixture was diluted with Et20 (1. 5L). After stirred for 5h, it was filtered through a pad of celite. The filtrate was concentrated to give an oil. The oil was purified on silica gel with Hexanes/EtOAc, 10: 1,6 : 1,3 : 1, and 1: 1 to give 24 g of desired product, 343-YW-203

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.

Reference£º
Patent; EISAI CO. LTD.; WO2003/76424; (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 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

Production of (S)-3-Hydroxy-1-(p-toluenesulfonyloxy)butane In the same manner as in the first step of Production Example 32, the desired compound (77.5 g) was obtained as light brown oil from (S)-1,3-butanediol (30.0 g) and p-toluenesulfonyl chloride (69.8 g). The thus-obtained oil was immediately subjected to the next step.

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.

Reference£º
Patent; Fujisawa Pharmaceutical Co., Ltd.; US6420409; (2002); 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 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

To (S)-propane diol (4.89 g, 64.2 mmol) in DCM (20 ml_) at -20 0C (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. The cold bath was allowed to expire while stirring for 26h. DCM was added and the reaction was washed with 1 N HCI, water, and brine. The organic layer was dried (MgSO4), 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).

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.

Reference£º
Patent; SCHERING CORPORATION; WO2009/5645; (2009); 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 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

Example 63 (R)-3- {2-CHLORO-4- [3- (4-CHLORO-2-PHENOXY-PHENOXY)-BUTOXY]-PHENYL}-PROPIONIC acid Step A (S) -Acetic acid 3-hydroxy-butyl ester; A mixture of (S)- (+)-1, 3-butanediol (10.0 g, 0.1 mol) and 2,4, 6-collidine (27 g, 0.2 mol) in DCM (100 mL) is cooled to-78 C. The reaction is then treated dropwise with acetyl chloride (10.4 g, 0.13 mol), and stirred for 2hr AT-78 C. The reaction is then allowed to warm to rt and stir for an additional hour. The reaction is then quenched with IN HCl and extracted with DCM. The organic layer is separated, washed with brine, and dried over NA2SO4. The organic is filtered, and the solvent is removed to afford 9.77 g (66%) of acetic acid 3-hydroxy-butyl ESTER. IH NMR (400 MHz, CDC13) ; MS (ES+) NILZ mass calcd for C6HI203 132, found 133 (M + 1)., 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.

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

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

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.

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.

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

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

To a stirred solution of 68 (S)-2-propanediol (1.00g, 13.14mmol) in 14 dichloromethane/69 pyridine (10:10 V/V) at -25C under argon was added dropwise 70 p-toluenesulfonyl chloride (2.51g, 13.14mmol) dissolved in 10mL of CH2Cl2 over a period of 2h. The mixture was stirred at -25C for 4h and then at room temperature for further 2h. After the reaction was completed, 30mL of CH2Cl2 were added and the mixture was shaken successively with ice-cold water, 1M 10mL 71 aqueous HCl, 15mL 72 water, saturated NaHCO3, and water, respectively. The organic phase was dried over MgSO4 and filtered and the solvent was removed under reduced pressure. The residue was purified by chromatography over silica gel using toluene/EtOAc (5/1) to give 73 product (1.70g, 56%) as white crystals. M.p: 33-35C, [alpha]D25=-12.05 (c 1, CHCl3). 1H NMR (CDCI3, ppm): delta 7.80 (d, 2H, J=8.0Hz, of OTs), 7.36 (d, 2H, J=8.0Hz, of OTs), 3.97-4.05 (m, 2H, -CHCH3-+CH2OTs (a)), 3.83-3.88 (m, 1H, CH2OTs (b)), 2.45 (s, 3H, -CH3 of OTs), 2.39 (s, 1H, OH), 1.15 (d, J=6.4Hz, 3H, -CHCH3), assignment was based on the 1H-13C HETCOR and 1H-1H COSY spectra

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.

Reference£º
Article; Meric, Nermin; Kayan, Cezmi; Guerbuez, Nevin; Karakaplan, Mehmet; Binbay, Nil Ertekin; Aydemir, Murat; Tetrahedron Asymmetry; vol. 28; 12; (2017); p. 1739 – 1749;,
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 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).

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.

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

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

Example 18C N-[(2Z)-3-butyl[1,3]thiazolo[4,5-c]pyridin-2(3H)-ylidene]-2-{[(2S)-2-hydroxypropyl]oxy}-5-(trifluoromethyl)benzamide (S)-propane-1,2-diol (52 mg, 0.68 mmol) in THF (1 mL) was treated with NaH (60percent dispersion; 27 mg, 0.68 mmol) at room temperature for 20 minutes. The mixture was cooled to 0¡ã C. and a solution of Example 18B (90 mg, 0.23 mmol) in THF (1 mL) was added. The mixture was allowed to warm to room temperature, and stirred for 4 hours. The mixture was diluted with saturated aqueous NaHCO3 (20 mL) and extracted with ethyl acetate (2.x.30 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered, and concentrated. The residue was purified by column chromatography using an Analogix.(R). Intelliflash280.(TM). (SiO2, 0-100percent ethyl acetate in hexanes) to afford 19 mg (19percent) of the title compound. 1H NMR (500 MHz, CDCl3) delta ppm 1.04 (t, J=7.48 Hz, 3H) 1.28 (d, J=6.41 Hz, 3H) 1.47-1.59 (m, 2H) 1.88-1.98 (m, 2H) 3.87 (t, J=8.85 Hz, 1H) 4.21-4.31 (m, 1H) 4.35 (dd, J=9.15, 2.75 Hz, 1H) 4.51-4.59 (m, 2H) 7.12 (d, J=8.85 Hz, 1H) 7.72 (dd, J=8.54, 2.14 Hz, 2H) 8.51 (d, J=1.83 Hz, 2H) 8.75 (s, 1H); MS (DCI/NH3) m/z 454 (M+H)+.

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.

Reference£º
Patent; ABBOTT LABORATORIES; US2011/144165; (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 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

To a yellow foamy solid 4 (131.77 g, 295.11 mmol) was added (S)-(+)-1,2-propanediol (296.0 ml) and purified water (866.0 ml).Stir and slowly cool after dissolving.Stirring crystallized, filtered and drained to give a crude product 5;The crude product 5 was directly recrystallized from methyl tert-butyl ether (900 ml) without drying.After filtering to get a fine 5;Without drying, recrystallize twice with methyl tert-butyl ether (900 ml) and filter.The filter cake is washed twice with methyl tert-butyl ether.After drying, it is dried in a drying oven at 45-50C.The second boutique 5 (116.37g, 231.22mmol),HPLC purity 99.94% [HPLC normalization method:Column Agilent SB-C18 (250¡Á4.6mm 5mum);The mobile phase is mobile phase A with acetonitrile-water-trifluoroacetic acid (30:70:0.025).The mobile phase B was acetonitrile-water-trifluoroacetic acid (90:10:0.025).Gradient elution (0?20 min: A 100%?70%, 20?40 min: A 70%?10%, 40?50 min: A 10%, 50?50.1 min:A 100%, 50.1 ? 60min: A 100%,) detection wavelength 220nm;Column temperature 30C; flow rate, 1.0 ml/min], yield 78.35%.

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.

Reference£º
Patent; Shanghai Modern Pharmaceutical Co., Ltd.; Zhang Guang; Shen Gang; Zou Lingyan; Fu Min; Wu Miaomiao; (13 pag.)CN107488156; (2017); 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