Analyzing the synthesis route of 453-20-3

453-20-3 3-Hydroxytetrahydrofuran 9960, aTetrahydrofurans compound, is more and more widely used in various fields.

453-20-3,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.453-20-3,3-Hydroxytetrahydrofuran,as a common compound, the synthetic route is as follows.

General procedure: To the mixture of 60% NaH (7.68 g, 0.053 mol), anhydrous THF (400 mL), (S)-tetrahydrofuran-3-ol (8.45 g, 0.096 mol) was added drop-wise at room temperature. The mixture was stirred at room temperature for 1 h a solution of compound 4a (10.0 g, 0.032 mol) in anhydrous THF (200 mL) was added via a dropping funnel over 1 h (the dropping funnel was rinsed with 15 mL of THF) at room temperature and the reaction mixture was stirred at room temperature for 2 h, the reaction was monitored by TLC. Then the solution was concentrated under a reduced pressure and the residue was poured into water with stirring, yielding a precipitate, then the mixture was filtered and washed with ice-water and ethanol, dried to afford compound 5b as yellow solid (9.8 g, 81.0%).

453-20-3 3-Hydroxytetrahydrofuran 9960, aTetrahydrofurans compound, is more and more widely used in various fields.

Reference£º
Article; OuYang, Yiqiang; Zou, Wensheng; Peng, Liang; Yang, Zunhua; Tang, Qidong; Chen, Mengzi; Jia, Shuang; Zhang, Hong; Lan, Zhou; Zheng, Pengwu; Zhu, Wufu; European Journal of Medicinal Chemistry; vol. 154; (2018); p. 29 – 43;,
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Simple exploration of 453-20-3

453-20-3, As the paragraph descriping shows that 453-20-3 is playing an increasingly important role.

453-20-3, 3-Hydroxytetrahydrofuran is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of tetrahydrofuran-3-ol (92.5 g, 1.05 mol) indichloromethane (2000 mL) was added pyridinium chlorochromate (454 g, 2.10 mol) and silica gel (500 g). The reaction mixture was heated to 40C. After 16 hours, the reaction mixture was filtered, and the filtrate was concentrated under reduced pressure to afford the crude residue. The residue was purified via chromatography on silica gel (methanol/DCM, linear gradient) to afford dihydrofuran-3(2H)-one.

453-20-3, As the paragraph descriping shows that 453-20-3 is playing an increasingly important role.

Reference£º
Patent; MERCK SHARP & DOHME CORP.; ALTMAN, Michael, D.; BIENSTOCK, Corey, E.; BUTCHER, John, W.; CHILDERS, Kaleen Konrad; DI FRANCESCO, Maria Emilia; DONOFRIO, Anthony; ELLIS, John Michael; FISCHER, Christian; HAIDLE, Andrew, M.; JEWELL, James, P.; KNOWLES, Sandra Lee; NORTHRUP, Alan, B.; OTTE, Ryan, D.; PETERSON, Scott, L.; SMITH, Graham Frank; WO2013/52394; (2013); A1;,
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Downstream synthetic route of 453-20-3

453-20-3, The synthetic route of 453-20-3 has been constantly updated, and we look forward to future research findings.

453-20-3, 3-Hydroxytetrahydrofuran is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

The compound tetrahydrofuran-3-ol (1.8 g, 20.0 mmol) was dissolved in DCM (50 mL), cooled to 0 C and then Et3N (3.0 mL, 22.0 mmo1) was added slowly to the reaction followed by MsCl (1.7 mL, 22.0 mmo 1) and a catalytic amount of DMAP were added successively, stirred overnight at room temperature, diluted with DCM (50 mL), washed with water (30 mL ¡Á 2) and separated. The organic phase was dried over anhydrous Na 2 SO 4, Concentration under reduced pressure gave the crude product as a light yellow oil (3.0 g, 90%) which was used directly in the next reaction without further purification.The compound 4-iodo-1H-pyrazole (776 mg, 4.0 mmol) was dissolved in dry DMF (50 mL), cooled to 0 C and then NaH (240 mg, 8.0 mmo 1, 80% NaH / mineral oil) was added and stirring was continued for 1 hour at 0 C. Then a solution of the oil obtained in the previous step (731 mg, 4.4 mmol) in DMF (10 mL) was added dropwise. The reaction was heated to 100 C. and reaction 24 After cooling to room temperature, the reaction was quenched by addition of water (0.5 mL), concentrated under reduced pressure and the residue suspended in DCM (50 mL). The resulting mixture was washed with water (30 mL), separated and the organic phase dried over anhydrous Na 2 SO 4 , Concentrated under reduced pressure to give the title compound as a white solid (1.0 g, 90%).

453-20-3, The synthetic route of 453-20-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; (88 pag.)CN104119331; (2018); B;,
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Some tips on 453-20-3

As the paragraph descriping shows that 453-20-3 is playing an increasingly important role.

453-20-3,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.453-20-3,3-Hydroxytetrahydrofuran,as a common compound, the synthetic route is as follows.

To a solution of 3-tetrahydrofuranol (1 g, 6.5 mmol) in DCM (10 mL) was added triethylamine (1.9 mL, 13.6 mmol). The reaction mixture was stirred for 15 minutes at room temperature. To the reaction mixture was added methanesulfonyl chloride (1.08 mL, 13.6 mmol) at 0C. The reaction mixture was stirred for a further 18 h. The reaction mixture was then quenched by addition of water, and diluted with EtOAc. The organic layer was washed with water and brine, dried over sodium sulphate and concentrated to yield the title compound (1.9 g, 88%). deltaEta (CDC13) 5.32 (m, 1H), 4.10-3.80 (m, 4H), 3.70 (s, 3H), 2.30-2.20 (m, 2H).

As the paragraph descriping shows that 453-20-3 is playing an increasingly important role.

Reference£º
Patent; UCB PHARMA S.A.; KATHOLIEKE UNIVERSITEIT LEUVEN, K.U.LEUVEN R&D; BROOKINGS, Daniel Christopher; FORD, Daniel James; FRANKLIN, Richard Jeremy; GHAWALKAR, Anant Ramrao; KULISA, Claire Louise; NEUSS, Judi Charlotte; REUBERSON, James Thomas; WO2013/68458; (2013); A1;,
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Some tips on 453-20-3

As the paragraph descriping shows that 453-20-3 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.453-20-3,3-Hydroxytetrahydrofuran,as a common compound, the synthetic route is as follows.,453-20-3

To a solution of (S)-4-(2-(((tert-butyldimethylsilyl)oxy)methyl)pyrrolidin-1-yl)-6-chloro-3- methyl-1H-pyrazolo[3,4-d]pyrimidine (435b) (150 mg, 0.39 mmol), triphenylphosphine (206 mg, 0.79 mmol), tert-butyl cis-4-hydroxycyclohexylcarbamate (127 mg, 0.59 mmol) in THF (3 mL) at 0 C was added dropwise DIAD (0.12 mL, 0.59 mmol). The reaction mixture was stirred at RT overnight, concentrated in vacuum and the residue obtained was purified by flash column chromatography [silica (12 g), eluting with EtOAc in hexane from 0-60%] to furnish tert-butyl ((tra5)-4-(4-((S)-2-(((tert-butyldimethylsilyl)oxy)methyl)pyrrolidin-l-yl)- 6-chloro-3-methyl-lH-pyrazolo[3,4-d]pyrimidin-l-yl)cyclohexyl)carbamate (435c) (150 mg, 66 % yield) as a white solid;1H MR (300 MHz, DMSO-d) delta 6.83 (d, J = 7.9 Hz, 1H), 4.54 – 4.38 (m, 2H), 3.90 – 3.63 (m, 4H), 3.32 – 3.22 (m, 1H), 2.55 (s, 3H), 2.13 – 1.75 (m, 10H), 1.39 (s, 1 1H), 0.82 (s, 9H), -0.05 (s, 6H); MS (ES+): 579.3 (M+l).

As the paragraph descriping shows that 453-20-3 is playing an increasingly important role.

Reference£º
Patent; BIOCRYST PHARMACEUTICALS, INC.; KOTIAN, Pravin, L.; BABU, Yarlagadda, S.; KUMAR, V., Satish; ZHANG, Weihe; LU, Peng-Cheng; RAMAN, Krishnan; (747 pag.)WO2018/232094; (2018); A1;,
Tetrahydrofuran – Wikipedia
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Analyzing the synthesis route of 453-20-3

453-20-3 3-Hydroxytetrahydrofuran 9960, aTetrahydrofurans compound, is more and more widely used in various fields.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.453-20-3,3-Hydroxytetrahydrofuran,as a common compound, the synthetic route is as follows.,453-20-3

To a solution of 3-hydroxytetrahydrofuran (200 mg, 1.55 mmol) in DCM (5 mL) was added Ms20 (539 mg, 3.10 mmol) and pyridine (367 mg, 4.65 mmol) at-10 C. After stirred at room temperature overnight, the reaction mixture was diluted with DCM (10 mL), washed with saturated NaHCO3, dried over anhydrous Na2504, and evaporated to dryness under reduced pressure to afford tetrahydrofuran-3-yl methanesulfonate 35 in 89% yield (285 mg).

453-20-3 3-Hydroxytetrahydrofuran 9960, aTetrahydrofurans compound, is more and more widely used in various fields.

Reference£º
Patent; CAPELLA THERAPEUTICS, INC.; LONG, Yun; (228 pag.)WO2017/53537; (2017); A1;,
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Tetrahydrofuran | (CH2)3CH2O – PubChem

Some tips on 453-20-3

453-20-3, As the paragraph descriping shows that 453-20-3 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.453-20-3,3-Hydroxytetrahydrofuran,as a common compound, the synthetic route is as follows.

To a solution of tetrahydrofuran-3-ol (500 mg, 5.68 mmcl) and Et3N (860 mg, 8.52 mmcl) inCH2CI2 (10 mL) at 0 C was added MsCI (842 mg, 7.39 mmol) dropwise. The reaction wasstirred at room temperature for 4 hours. The reaction mixture was diluted with CH2CI2 (150mL), washed with sat. NaHCO3 (50 mL), dried over Na2SO4 and concentrated to give the title compound (700 mg, 74%) as yellow oil.1H NMR (300 MHz, CDCI3): oe 5.36-5.31 (m, IH), 4.06-3.86 (m, 4H), 3.06 (s, 3H), 2.29-2.22 (m, 2H).

453-20-3, As the paragraph descriping shows that 453-20-3 is playing an increasingly important role.

Reference£º
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; GLAXOSMITHKLINE (CHINA) R&D COMPANY LIMITED; DING, Xiao; REN, Feng; SANG, Yingxia; XING, Weiqiang; ZHAN, Yang; ZHAO, Baowei; (357 pag.)WO2018/137593; (2018); A1;,
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Brief introduction of 453-20-3

453-20-3 3-Hydroxytetrahydrofuran 9960, aTetrahydrofurans compound, is more and more widely used in various.

453-20-3, 3-Hydroxytetrahydrofuran is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,453-20-3

Description 20 : Dihydro-3(2H)-furanone; A mixture of 3-hydroxytetrahydrofuran (3.0 g, 0.034 mol) and pyridinium chlorochromate (14.7 g, 0.068 mol) in DCM (100 ml) was stirred at room temperature overnight. The title product was obtained by pouring the crude product through a silica pad using ethyl acetate as the eluent. The title product was obtained from 2 elutions (2.29 g; 79%). 1H NMR (CDCI3) delta: 2.50 (2H, t), 3.87 (2H, s), 4.26 (2H, t).

453-20-3 3-Hydroxytetrahydrofuran 9960, aTetrahydrofurans compound, is more and more widely used in various.

Reference£º
Patent; GLAXO GROUP LIMITED; WO2006/67430; (2006); A1;,
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Simple exploration of 453-20-3

As the paragraph descriping shows that 453-20-3 is playing an increasingly important role.

453-20-3,453-20-3, 3-Hydroxytetrahydrofuran is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of tetrahydro-furan-3-ol (9.0 g, 79 mmol) and triethyl amine (20 mL, 176 mmol) in THF (200 mL) was added methanesulfonyl chloride (12.9 g, 113 mmol) at 0 C. The mixture was stirred overnight and then evaporated to dryness. The residue was extracted with EtOAc (3*300 mL) and washed with saturated, aqueous NaRCO3. The organic layer was dried over Na2SO4 and evaporated to dryness to give methanesulfonic acid tetrahydro-furan-3-yl ester as a yellow viscous liquid (12.4 g. 94%) which was used without further purification.

As the paragraph descriping shows that 453-20-3 is playing an increasingly important role.

Reference£º
Patent; H. Lundbeck A/S; US2012/252853; (2012); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem

Downstream synthetic route of 453-20-3

The synthetic route of 453-20-3 has been constantly updated, and we look forward to future research findings.

453-20-3, 3-Hydroxytetrahydrofuran is a Tetrahydrofurans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,453-20-3

To a suspension of sodium hydride (1.2 equiv, 60% by weight in mineral oil) in THF (0.3 M) under nitrogen atmosphere was added tetrahydrofuran-3-ol (1.5 equiv) in THF (0.6 M) at 0 C. The resulting reaction mixture was stirred at 0 C. for 20 min. A solution of 6-(2,4-dichloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methylbenzo[d]oxazole (1 equiv) in THF (0.6 M) was added and the resulting reaction mixture was stirred at room temperature for 3 h. The reaction mixture was quenched with saturated aqueous ammonium chloride solution (0.6 M) and the organic solvents were removed under reduced pressure. The resulting residue was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and filtered. The filtrate was evaporated under reduced pressure and the crude product was purified by silica gel chromatography (15% ethyl acetate in petroleum ether) to afford the title compound (83% yield). MS (ESI) m/z 501.1 [M+H]+.

The synthetic route of 453-20-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Signal Pharmaceutical LLC; Calabrese, Andrew Antony; Jeffy, Brandon; Robinson, Dale; Zhu, Dan; Huang, Dehua; Elsner, Jan; Boylan, John; Tehrani, Lida; Nagy, Mark A.; Moghaddam, Mehran Fallah; Raheja, Raj Kumar; Erdman, Paul; Narla, Rama K.; Harris, Roy L.; Tran, Tam Minh; Riggs, Jennifer; Ning, Yuhong; US2014/200206; (2014); A1;,
Tetrahydrofuran – Wikipedia
Tetrahydrofuran | (CH2)3CH2O – PubChem