Day: November 5, 2020

90319-52-1, (R)-4-Phenyloxazolidin-2-one is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 35 (R,E)-3-(3- (3-benzyloxy) phenyl) acryloyl)-4-phenyl oxazolidin-2-one The m-benzyloxy cinnamic acid (90g, 354mmol) was dissolved in dichloromethane (25ml), oxalyl chloride (45ml) was added therein and it was reacted at room temperature for 5 hours, then the reaction solution was concentrated to remove the solvent and oxalyl chloride for further use; 4(R)-phenyl-2-oxazolidinone (57g, 350mmol) was dissolved in dichloromethane, the mixture was cooled to 0¡ãC, and 4-dimethylamino pyridine (4.3g, 35mmol) and triethylamine (76 mL, 525mmol) was added, then the solution of m-benzyloxy cinnamic acid in dichloromethane was added. After that, the reaction was continued for 8 hours and quenched with saturated ammonium chloride solution, then the reaction solution was separated, the dichloromethane layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, concentrated and recrystallized with petroleum ether and ethyl acetate to give a white solid 144g, yield: 95percent. The HNMR spectrum data is the same as that in, 90319-52-1

The synthetic route of 90319-52-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Shanghai Institute Materia Medica, Chinese Academy Of Sciences; Topharman Shanghai Co., Ltd.; ZHANG, Qiang; ZHANG, Rongxia; TIAN, Guanghui; LI, Jianfeng; ZHU, Fuqiang; JIANG, Xiangrui; SHEN, Jingshan; EP2671878; (2013); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

90319-52-1, (R)-4-Phenyloxazolidin-2-one is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a stirred solution of (is)-3-(2,2-dimethyltetrahydro-2H-pyran-4-yl)acrylic acid (9 g, 48.9 mmol) in 350 mL of THF was added TEA (7.49 mL, 53.7 mmol). The resulting solution was stirred under 2 atmosphere and cooled to -10 ¡ãC (ice/salt water bath). Pivaloyl chloride (6.37 mL, 51.8 mmol) was added dropwise over 5 min and a thick precipitate formed. This suspension (A) was stirred at -10 ¡ãC for 15 min then cooled to -78 ¡ãC. In a separate flask, (R)-4-phenyloxazolidin-2-one (9.01 g, 55.2 mmol) was dissolved in THF (150 mL) and the solution was stirred and cooled to -78 ¡ãC under 2 atmosphere. n-BuLi (20.52 mL of a 2.5 M solution in hexane) was added dropwise over 5 min and a precipitate formed. This suspension (B) was stirred at -78 ¡ãC for 10 min. Suspension A (cooled at -78 ¡ãC) was added to suspension B via cannula over a period of 5 min. The resulting mixture was stirred at -78 ¡ãC for 10 min, then the cooling bath was removed and the mixture was stirred for 1.5 h while it gradually warmed to RT. The reaction mixture was poured into a 1000 mL Erlenmeyer flask and was diluted with EtOAc (400 mL). The resulting solution was extracted with water (2 x 300 mL), brine (300 mL), then dried over sodium sulfate, filtered, and concentrated in vacuo. The crude product was purified on a 220 g silica gel column eluting with a gradient of 0-60percent ethyl acetate in hexanes. The fractions containing product were combined and the solvents were removed under reduced pressure to afford to give the title compound, MS: m/z = 330 (M+H)+., 90319-52-1

As the paragraph descriping shows that 90319-52-1 is playing an increasingly important role.

Reference£º
Patent; MERCK SHARP & DOHME CORP.; MSD R&D (CHINA) CO., LTD.; WILLIAMS, Peter, D.; MCCAULEY, John, A.; BUNGARD, Christopher, J.; BENNETT, David Jonathan; WADDELL, Sherman, T.; MORRIELLO, Gregori, J.; CHANG, Lehua; DWYER, Michael, P.; HOLLOWAY, M. Katharine; CRESPO, Alejandro; CHU, Xin-Jie; WISCOUNT, Catherine; LOUGHRAN, H. Marie; MANIKOWSKI, Jesse, J.; SCHULZ, Jurgen; KEERTIKAR, Kartik, M.; HU, Bin; ZHONG, Bin; JI, Tao; WO2015/138220; (2015); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.99395-88-7,(S)-4-Phenyloxazolidin-2-one,as a common compound, the synthetic route is as follows.

The compounds of formula 21.2g taken with 110ml of DMF was dissolved and replaced with nitrogen, cooled to -10 ~ 0 C under nitrogen, temperature control, input portionwise 16g of lithium hydride, insulation 0.5h, slowly dropwise benzyl chloroformate ester 30.2g, control temperature -10 ~ 0 C, after the addition was complete insulation 1h, warmed to 20 ~ 25 C, into S-4- phenyl-2-oxazolidinone 15.5g, feeding ended, insulation, the reaction was complete, water and methyl tert-butyl ether extracts, standing layer, the organic layer was washed with saturated brine, evaporated under reduced pressure to give an oil. With a mixture of ethyl acetate and hexane to crystallize with stirring, suction filtered and washed with hexane, dried in vacuo to give a white solid product 38.8g, yield 92.9%, HPLC purity 94%. Without further purification, can be used directly in the next step., 99395-88-7

99395-88-7 (S)-4-Phenyloxazolidin-2-one 730424, aoxazolidine compound, is more and more widely used in various fields.

Reference£º
Patent; Zhejiang Jiuzhou Pharmaceutical Co., Ltd; ZHU, GUOLIANG; LI, YUNGUANG; YANG, LIJUN; SUN, LIGUO; CHEN, XIANGYUAN; (8 pag.)CN105461649; (2016); A;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

99395-88-7, (S)-4-Phenyloxazolidin-2-one is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

[0728] To a solution of 2-(1-(tert-butoxycarbonyl)-3-vinylazetidin-3-yl)acetic acid (40-3, 1.9 g, 8.12 mmol) in anhydrous THF (30 mL) and cooled to -15 oC was added triethylamine (1.2 mL, 8.93 mmol), followed by dropwise addition of pivaloyl chloride (1.04 mL, 8.52 mmol). The heterogeneous mixture was stirred for 20 min at 0 oC, then re-cooled to -78 oC and stirred for 15 min (solution 1). In a separate flask, (S)-(+)-4-phenyl-2-oxazolidinone (1.32 g, 8.12 mmol) was dissolved in anhydrous THF (30 mL) and cooled to -78 oC. A solution of n-butyl lithium (2.5 M in hexane, 3.2 mL, 8.12 mmol) was added dropwise followed by dropwise addition (15 min) of the mixed anhydride solution (solution 1). The resulting mixture was further stirred for 10 min at -78 oC at which time it was warmed to 0 oC and stirred for 40 min. The reaction mixture was quenched with 10% citric acid (13 mL) and extracted with ethyl acetate (120 mL x 2). The combined organic layers were washed with brine (50 mL x 3), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude residue was purified by CombiFlash column chromatography on silica gel (0- 40% EtOAc in hexane) to afford (S)-4-phenyl-3-(2-(1- (tert-butoxycarbonyl)-3-vinylazetidine-3-yl)acetyl)oxazolidin-2-one (40-4, 2.7 g, 87% yield) as white solid.1H NMR (250 MHz, CDCl3) delta ppm 1.41 (s, 9 H), 3.45 (s, 2 H), 3.77 (t, J = 10.71 Hz, 1 H), 3.82 – 3.93 (m, 2 H), 4.29 (dd, J = 8.90, 3.74 Hz, 1 H), 4.70 (t, J = 8.84 Hz, 1 H), 4.95 – 5.12 (m, 2 H), 5.40 (dd, J = 8.62, 3.57 Hz, 1 H), 6.03 (dd, J = 17.41, 10.71 Hz, 1 H), 7.24 – 7.44 (m, 5 H). MS: [M+H]+ = 386.6.

99395-88-7, As the paragraph descriping shows that 99395-88-7 is playing an increasingly important role.

Reference£º
Patent; ACHAOGEN, INC.; COHEN, Frederick; KONRADI, Andrei W.; CHOI, Taylor Ann Joo; MACHAJEWSKI, Timothy D.; KANE, Timothy Robert; HILDEBRANDT, Darin James; (351 pag.)WO2017/223349; (2017); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.99395-88-7,(S)-4-Phenyloxazolidin-2-one,as a common compound, the synthetic route is as follows.

To a precooled (0 C) solution of (S)-3-(4-chlorophenyl)-3-(5- (trifluoromethyl)pyridin-3-yl)acrylicacid (1.30 g, 3.94 mmol) in THF (10.0 mL) was added pivolyl chloride (570 mg, 4.73 mmol), DMAP (cat), followed by triethylamine (796 mg, 7.88 mmol) and stirred for 1 h. In another precooled (0 C) suspension of 60% NaH (7.88 mmol) in THF, was added (S)-4-phenyloxazolidin-2-one (772 mg, 4.73 mmol) in THF (10.0 mL) drop- wise and stirred at 0 C for 1 h. The mixed anhydride was added to the reaction mixture and stirred for another 5 h. The reaction mixture was quenched with water (20.0 mL) and extracted with EtOAc (2 x 100 mL). The combined EtOAc extracts were washed with brine (100 mL), dried (Na2S04), filtered, and concentrated under reduced pressure. The residue was purified on 12 g S1O2 using a gradient elution of 0-20% EtOAc in hexanes. Fractions containing the product were combined and concentrated under reduced pressure to provide the product (1.40 g, 76%) as a white solid. MS: m/z = 475 (M+H+)., 99395-88-7

99395-88-7 (S)-4-Phenyloxazolidin-2-one 730424, aoxazolidine compound, is more and more widely used in various fields.

Reference£º
Patent; MERCK SHARP & DOHME CORP.; MSD R&D (CHINA) CO., LTD; WILLIAMS, Peter D.; MCCAULEY, John A.; BENNETT, David Jonathan; BUNGARD, Christopher J.; CHANG, Lehua; CHU, Xin-Jie; DWYER, Michael P.; HOLLOWAY, M. Katharine; KEERTIKAR, Kartik M.; LOUGHRAN, H. Marie; MANIKOWSKI, Jesse J.; MORRIELLO, Gregori J.; SHEN, Dong-Ming; SHERER, Edward C.; SCHULZ, Jurgen; WADDELL, Sherman Tim; WISCOUNT, Catherine M.; ZORN, Nicolas; TUMMANAPALLI, Satyanarayana; SIVALENKA, Vijayasaradhi; HU, Bin; JI, Tao; ZHONG, Bin; WO2015/13835; (2015); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.99395-88-7,(S)-4-Phenyloxazolidin-2-one,as a common compound, the synthetic route is as follows.

MTBE was added to the 1L reaction flask, 69.78 g pentanoic acid (Compound 1a, 1.2 eq.), Sodium bicarbonate (19.1 g, 2.7 eq), nitrogen was cooled to -40 .Specter pivaloyl chloride was slowly added dropwise 82.38 (compound 3a, 1.2 equiv).Kept stirring at -40 10 hours, 31.38 g of anhydrous lithium chloride (1.3 eq.).(S) -4- phenyl-oxazolidin-2-one (compound 2b, 92.91 g) was formulated into a solution of methyl t-butyl ether, was slowly added dropwise to the reaction solution.Warmed to 35 ~ 40 , stirring was continued for 4 hours.Filtered, the filtrate was added sodium hydroxide solution, and sufficiently stirred, the solvent was evaporated under reduced pressure and extracted with a solvent.The organic layer was washed with dilute hydrochloric acid, saturated brine, dried, filtered, and solvent removal, to obtain 125 g of colorless oil (S) -4- phenyl-3-pentanoyl-oxazolidin-2-one (Compound 4b, 90% purity, 89% yield)., 99395-88-7

The synthetic route of 99395-88-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Shanghai Huaxingxi Pharmaceutical Technology Co., Ltd; Fan, Penggao; Rao, Weijun; Jiang, Rongying; (11 pag.)CN106008411; (2016); A;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.99395-88-7,(S)-4-Phenyloxazolidin-2-one,as a common compound, the synthetic route is as follows.

To a solution of 69.0 g (615 mmol) of 5-hexynoic acid and 214 mL (1540 mmol) of triethylaraine in 1.0 L of ar ydrous tetrahydrofuran at -25C under an atmosphere of nitrogen was added 83.0 mL (677 mmol) of trimethylacetyl chloride over 20 min. Upon addition a white precipitate formed and the resulting suspension was stirred for 2 h. Next, 28.7 g (677 mmol) of anhydrous lithium chloride and 100.0 g (615.0 mmol) of (4S)-4-phenyl-l,3-oxazolidin-2-one were added sequentially and the mixture was allowed to gradually warm to ambient temperature over 12 h. All volatiles were removed in vacuo and the residue was diluted with water (1 L) and extracted with ethyl acetate (3 x 300 mL). The combined organic layers were washed with brine (250 mL), dried over magnesium sulfate, filtered and concentrated in vacuo. The crude residue was purified by silica gel chromatography eluting with a 5-50% ethyl acetate in hexanes gradient to afford the title compound as a colorless solid (135 g, 85.4%). 1H NMR (500 MHz, CDC13): delta 7.40-7.37 (m, 2H), 7.36-7.32 (m, 1H), 7.31-7.28 (m, 2H), 5.42 (dd, J= 8.9, 3.7 Hz, 1H), 4.69 (t, J= 8.9 Hz, IE), 4.28 (dd, J= 92, 3.7 Hz, 1H), 3.13-3.02 (m, 2H), 2.24-2.21 (m, 2H), 1.94 (t, J= 2.6 Hz, 1H), 1.84 (quintet, J- 7.1 Hz, 2H). LC-MS: m/z (ES) 258.2 (MH)+., 99395-88-7

As the paragraph descriping shows that 99395-88-7 is playing an increasingly important role.

Reference£º
Patent; MERCK SHARP & DOHME CORP.; BERGER, Richard; EDMONDSON, Scott, D.; HARPER, Bart, H.; WO2011/137054; (2011); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.90319-52-1,(R)-4-Phenyloxazolidin-2-one,as a common compound, the synthetic route is as follows.

Step 4. (R, ?)-4-Phenyl-3-(3-(2,2- -4-yl)acryloyl)oxazolidin-2-one To the solution of (is)-3-(2,2-dimethyltetrahydro-2H-pyran-4-yl)acrylic acid (9 g, 48.9 mmol) in 350 ml of THF was added TEA (7.49 mL, 53.7 mmol) and the resulting solution was stirred under 2 atmosphere and cooled to -10¡ãC (ice/salt water bath). Piv-Cl (6.37 mL, 51.8 mmol) was then added dropwise via syringe over 5 minutes, a thick precipitate formed, this resulting suspension (A) was stirred at -10¡ãC for 15 min then cooled to -78¡ãC. (R)-4-phenyloxazolidin-2- one (9.01 g, 55.2 mmol) was charged to a separate 500 mL round bottom flask and was dissolved in THF (150 mL) and the resulting solution was stirred and cooled to -78¡ãC under 2 atmosphere. n-BuLi (20.52 mL of a 2.5 M solution in hexane) was then added dropwise via syringe over 5 minutes, to which a precipitate formed and this resulting suspension (B) was stirred at -78¡ãC for 10 min. Then solution A (cooled at -78¡ãC) was then added to solution B via cannula over about 5 minutes. The resulting mixture was then stirred at -78¡ãC for 10 minutes and then the cooling bath was removed and the mixture was stirred for 1.5 h while it gradually warmed up to room temperature. The reaction mixture was poured into a 1000 mL Erlenmeyer flask and was diluted with EtOAc (400mL). This solution was then extracted with water (2 x 300 mL) and washed by brine (300 mL), then dried over sodium sulfate, filtered, and stripped in vacuo to give a clear oil. The oil was taken up in DCM and purified via Biotage (RediSep 220 g silica gel) eluting with a gradient of 0-60percent ethyl acetate in hexane. The tubes containing the product were collected and the solvent removed under reduced pressure to afford the product as a white solid (10.12 g, 62.9percent). MS: m/z = 330 (M+H+)., 90319-52-1

90319-52-1 (R)-4-Phenyloxazolidin-2-one 730425, aoxazolidine compound, is more and more widely used in various fields.

Reference£º
Patent; MERCK SHARP & DOHME CORP.; MSD R&D (CHINA) CO. LTD.; WILLIAMS, Peter, D.; MCCAULEY, John, A.; BENNETT, David, J.; BUNGARD, Christopher, J.; CHANG, Lehua; CHU, Xin-Jie; DWYER, Michael, P.; HOLLOWAY, M. Katherine; KEERTIKAR, Kartik, M.; LOUGHRAN, H. Marie; MANIKOWSKI, Jesse, J.; MORRIELLO, Gregori, J.; SHEN, Dong-Ming; SHERER, Edward, C.; SCHULZ, Jurgen; WADDELL, Sherman Tim; WISCOUNT, Catherine, M.; ZORN, Nicolas; SATYANARAYANA, Tummanapalli; VIJAYASARADHI, Sivalenka; HU, Bin; JI, Tao; ZHONG, Bin; WO2015/17393; (2015); A2;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.99395-88-7,(S)-4-Phenyloxazolidin-2-one,as a common compound, the synthetic route is as follows.

Add 10 ml of dichloromethane, 500 ml of triethylamine (3.6 mol), and phenyloxazolidinone 163 g to a 5-liter four-necked bottle.(1 mol), propionic acid 80 g (1.1 mol), 300 g (1 mol)2-chloropyridine methyl p-toluenesulfonate salt 1000 ml of dichloromethaneThe solution was added and stirred at 25 C for 5 hours. TLC showed the reaction was complete, and the mixture was extracted with water and washed with water and saturated brine.The organic phase was dried over anhydrous sodium sulfate, concentrated, and then recrystallised to give product 200 g, yield: 91.3%, HPLC purity >99%., 99395-88-7

As the paragraph descriping shows that 99395-88-7 is playing an increasingly important role.

Reference£º
Patent; Shanghai Lark Pharmaceutical Technology Co., Ltd.; Shen Xin; Yang Jidong; Hu Xiaochuan; Li Feng; (6 pag.)CN109020914; (2018); A;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.99395-88-7,(S)-4-Phenyloxazolidin-2-one,as a common compound, the synthetic route is as follows.

To a solution of sodium hydride (13.5 g) in tetrahydrofuran (920 mL) was added (4S)-4-phenyl-1,3-oxazolidin-2-one (50 g) portionwise at room temperature, and the resulted mixture was stirred for 1 hour. This reaction solution is referred to as Solution A. In a separate reaction vessel, a solution of chloroacetyl chloride (36.6 mL) in tetrahydrofuran (308 mL) was cooled to 0 C, and the above Solution A was added dropwise in about 5 mL for each portion. After stirred at 0 C for 1 hour, water (300 mL) was slowly added to the reaction solution. The resulted mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, then dried over sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure, the obtained residue was dissolved in dichloromethane (500 mL). To the resulted solution was added p-methoxybenzylthiol (47.2 g) at room temperature, followed by adding triethylamine (64 mL) dropwise using a dropping funnel over 1.5 hours. The resulted solution was then stirred at room temperature overnight. Water (300 mL) and dichloromethane (100 mL) were added to the reaction solution to separate the organic layer and the organic layer was then washed with brine. The organic layer was dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane = 1/5 ? 1/3 ? 1/2) to obtain the title compound (90 g, 82% yield for 2 steps). The NMR data of this compound is shown below. 1H-NMR (400 MHz, CDCl3): delta (ppm) = 3.49-3.61 (m, 3H), 3.77-3.81 (m, 1H), 3.78 (s, 3H), 4.28 (dd, 1H, J = 8.9, 3.9 Hz), 4.62 (dd, 1H, J = 8.9 Hz), 5.43 (dd, 1H, J = 8.9, 3.9 Hz), 6.78-6.81 (m, 2H), 7.14-7.18 (m, 2H), 7.34-7.43 (m, 5H)., 99395-88-7

The synthetic route of 99395-88-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Teijin Pharma Limited; EP2133347; (2009); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem