Category: 24621-61-2

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.

The flask was charged with (S) -butane-1,3-diol (1.00 g, 11.10 mmol) in dichloromethane (DCM) (27 mL),Triethylamine (1.347 g, 13.32 mmol),4-Dimethylaminopyridine (0.136 g, 1.110 mmol) and 4-methylbenzene-1-sulfonyl chloride (2.327 g, 12.21 mmol) were added. The reaction was stirred at room temperature for 1 hour.Quench the reaction with saturated NH 4 Cl,Extracted with DCM. The organic portion was dried over MgSO 4, filtered and concentrated under reduced pressure to give a residue which was purified by silica gel chromatography eluting with 0-50% ethyl acetate / heptane to give the product (0. 288 g, 1.179 mmol, yield 10.62%).

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; 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 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

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%).

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
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

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

(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).

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; 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 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 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

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; 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 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,(S)-Butane-1,3-diol,24621-61-2,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 (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

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; 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

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).

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; 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

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.

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., 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; 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, 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 4 Synthesis of Maytansinoid 4k,l (d) S-1,3-Di-O-p-toluenesulfonyl-butane 22: A solution of S-(-)-1,3-butanediol (21, 2.00 g (22.22 mmol) in a mixture of dry pyridine (40 mL) and dry toluene (60 mL) was treated with p-toluenesulfonyl chloride (12.70 g, 66.84 mmol) under argon at 0 C. After stirring at 0 C. for 5 min. followed by stirring at room temperature for 2 h, the mixture was evaporated under vacuum. The residue was redissolved in ethyl acetate, washed with 0.1 M aqueous NaHCO3, and saturated NaCl. The organic layer was separated, dried over MgSO4, filtered and evaporated. The residue was purified by chromatography over silica gel, eluding with 1:2 ethyl acetate/hexane to give 6.25 g (71%) of the title product 22 Rf=0.40 (1:1 EtOAc/hexane); 1H NMR (CDCl3) 7.76 (dd, 4H, J=1.0, 8.0 Hz), 7.35 (dt, 4H, J=0.4, 8.0+8.0 Hz), 4.70 (m, 1H), 4.03 (m, 1H), 3.94 (m, 1H), 2.46 (s, 6H), 1.92 (m, 2H), 1.26 (d, 3H, J=6.3 Hz); 13C NMR 145.17, 133.00, 130.11, 128.12, 127.91, 76.28, 66.21, 36.08, 21.86, 21.06; MS: 420.99 (M+Na)+.

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; IMMUNOGEN, INC.; US2004/235840; (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, 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

The flask was charged with (S) -butane-1,3-diol (1.00 g, 11.10 mmol) in dichloromethane (DCM) (27 mL),Triethylamine (1.347 g, 13.32 mmol),4-Dimethylaminopyridine (0.136 g, 1.110 mmol) and 4-methylbenzene-1-sulfonyl chloride (2.327 g, 12.21 mmol) were added. The reaction was stirred at room temperature for 1 hour.Quench the reaction with saturated NH 4 Cl,Extracted with DCM. The organic portion was dried over MgSO 4, filtered and concentrated under reduced pressure to give a residue which was purified by silica gel chromatography eluting with 0-50% ethyl acetate / heptane to give the product (0. 288 g, 1.179 mmol, yield 10.62%).

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; 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