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.

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)+., 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; 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

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.

Preparation of (3S)-1-p-Toluenesulfonyloxy-3-triethylsilyloxy-butane (2b); To a stirred, solution of the(S)-(+)-1,3-butanediol 1b (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.

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; WISCONSIN ALUMNI RESEARCH FOUNDATION; US2012/283228; (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

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, 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, 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, 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 INEL SynthesisPreparation 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 colorless oil.To a stirred solution of the tosylate (2.31 g, 9.5 mmol) and 2,6-lutidine (1.2 mL, 1.12 g, 10.5 mmol) in anhydrous methylene chloride (15 mL) triethylsilyl trifluoromethanesulfonate (2.1 mL, 2.51 g, 9.5 mmol) was added at -50 C. The reaction mixture was allowed to warm to room temperature (4 h) and stirring was continued for additional 20 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 (97:3) to afford the product 2 (2.71 g, 80% yield) as a colorless oil:[alpha]D+18.0 (c 2.38, CHCl3); 1H NMR (400 MHz, CDCl3) delta7.77 (2H, d, J=8.2 Hz, o-HTs), 7.33 (2H, d, J=8.2 Hz, m-HTs), 4.10 (2H, t, J=6.1 Hz, 1-H2), 3.90 (1H, m, 3-H), 2.43 (3H, s, McTs), 1.72 (2H, m, 2-H2), 1.10 (3H, d, J=6.2 Hz, 4-H3), 0.88 (9H, t, J=8.0 Hz, 3¡ÁSiCH2CH3), 0.50 (6H, q, J=8.0 Hz, 3¡ÁSiCH2CH3); 13C NMR (100 MHz) delta 144.62 (s, p-CTs), 133.03 (s, i-CTs), 129.72 (d, m-CTs), 127.82 (d, o-CTs), 67.78 (t, C-1), 64.46 (d, C-3), 38.47 (t, C-2), 23.82 (q, C-4), 21.52 (q, MeTs), 6.71 (q, SiCH2CH3), 4.77 (t, SiCH2CH3); MS (EI) m/z 359 (5, MH+), 329 (87, M+ -C2H5), 259 (100), 233 (54), 197 (50), 179 (74), 163 (40), 149 (48), 135 (38), 115 (53), 91 (71); exact mass calculated for C15H25O4SSi (M+ -C2H5) 329.1243, found 329.1239.

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; WISCONSIN ALUMNI RESEARCH FOUNDATION; US2007/191316; (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.

p-Toluenesulfonyl chloride (381 mg, 1 .68 mmol) was dissolved in anhydrous DCM (10 mL) at RT under N2. (s)-(+)-1 ,3-butandiol (300 muIota_, 3.33 mmol) was added followed by NEt3 (450 muIota_, 3.33 mmol) and the solution stirred for 18 h. The solution was partitioned with H2O (15 mL) and extracted with DCM (3 x 10 mL), Combined organic fractions were dried by phase separator and the mixture loaded onto silica for purification by flash chromatography. The desired compound A32 was isolated as a clear oil (144 mg, 29%); -NMR (400 MHz, DMSO-c/6): delta 7.78 (d, J = 8.0 Hz, 2H), 7.48 (d, J = 8.0 Hz, 2H), 4.56 (d, J = 5.0 Hz, 1 H), 4.12-4.00 (m, 2H), 3.65-3.57 (m, 1 H). 2.43 (s, 3H), 1 .69-1 .54 (m, 2H), 1 .00 (d, J = 6.0 Hz, 3H).

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; IMPERIAL INNOVATIONS LIMITED; SCHNEIDER, Michael; NEWTON, Gary; CHAPMAN, Katie; PERRIOR, Trevor; JARVIS, Ashley; LOW, Caroline; AQIL, Rehan; FISHER, Martin; BAYFORD, Melanie; CHAPMAN, Nicholas; MARTIN, Nicholas; REISINGER, Tifelle; NEGOITA-GIRAS, Gabriel; (260 pag.)WO2019/73253; (2019); 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