Tag: M.W:100-200

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

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.

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

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

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

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

A flame-dried 1 L round bottomed flask containing an MTBE solution of 6 (2.8 g, 33 mmol), and 800 mL of THF was chilled by a cold bath at -30 C. (dry ice/30% ethanol in ethylene glycol). The mixture was allowed to stir under nitrogen atmosphere. Distilled triethylamine (12.2 g, 17.0 mL, 120 mmol), and pivaloyl chloride (6.0 g, 6.2 mL, 50 mmol) were added sequentially, and stirring at -30 C. was continued for one hour. LiCl (7.0 g, 170 mmol) was added. After five minutes, (S)-4-phenyloxazolidinone (9.8 g, 60 mmol), and 4-dimethylamino pyridine (408 mg, 3.35 mmol) were added. The whole reaction mixture was allowed to stir overnight at room temperature. The solvents were removed under reduced pressure, and the residue was partitioned between 300 mL of CH2Cl2 and 300 mL water. The aqueous layer was extracted twice with 300 mL portions of CH2Cl2, and the combined organics were dried (Na2SO4), filtered, and concentrated. The residue was chromatographed on silica gel. The initial eluent was 1:1:9 CH2Cl2:ethyl acetate:hexane, followed by elution with 1:3:7 CH2Cl2:ethyl acetate:hexane. The yield of 7 was 7.20 g (31.5 mmol, 95%). Compound 7 is a white solid. mp=118-119 C., [alpha]D+140.0 (c 1.00, THF)., 99395-88-7

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

Reference£º
Patent; University of Delaware; US2009/23916; (2009); 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

R-4-phenyl-2-oxazolidone (4 g, 24.5 mmol) was dissolved in 50 mL of dichloromethane, and then triethylamine (5.2 mL, 1.5 eq) was added therein. Subsequently, 2-fluoro-propionyl chloride (1.3 eq) was slowly added dropwise at 0¡ã C.5¡ãAfter the raw materials were completely reacted indicating by TLC, filtering the solid, drying the organic phase by concentration, then 20 mL of methanol was added. The resulting mixture was stirred for 3 h and filtered to give 5 g white solid in a yield of 86.0percent., 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; TOPHARMAN SHANGHAI CO., LTD.; SHANGHAI INSTITUTE OF MATERIA MEDICA, CHINESE ACADEMY OF SCIENCES; TOPHARMAN SHANDONG CO., LTD.; Wang, Guan; Jiang, Xiangrui; Gong, Xudong; Chen, Weiming; Zhu, Fuqiang; Zhang, Rongxia; Zhao, Xianguo; US2015/284351; (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.90319-52-1,(R)-4-Phenyloxazolidin-2-one,as a common compound, the synthetic route is as follows.

To a stirred solution of 4 (2 kg, 8 mol) in CH2Cl2 (2 L) was added oxalyl chloride (1.4 L, 16 mol) dropwise at 0 ¡ãC. The resulting solution was stirred at room temperature for another 4 h and concentrated in vacuo. To a stirred solution of (R)-4-phenyloxazolidin-2-one (1.3 kg, 8 mol) and TEA (1.7 L, 12 mol) in CH2Cl2 (4.8 L) at 0 ¡ãC was added the substituted cinnamic chloride in CH2Cl2 (800 mL) dropwise. The mixture was stirred at 0 ¡ãC for 1 h and then raised to room temperature for 3 h when a saturated solution of NH4Cl (600 mL) was added. The aqueous layer was separated, and the organic solution was washed with water (600 mL .x. 3), brine (800 mL), and dried over Na2SO4. The organic solution was evaporated and 2.9 kg of 5 was obtained after recrystallization in EtOH in 93percent yield, mp 143-145 ¡ãC, (c 1.0, CHCl3). 1H NMR (300 MHz, CDCl3): delta 7.86 (d, J = 15.5 Hz, 1H), 7.75 (d, J = 15.3 Hz, 1H), 7.30-7.50 (m, 11H), 7.23 (m, 2H), 7.03 (dd, J = 2.3, 8.6 Hz, 1H), 5.64 (dd, J = 4.0, 9.0 Hz, 1H), 5.15 (s, 2H), 4.85 (t, J = 8.9 Hz, 1H), 4.36 (dd, J = 3.9, 8.8 Hz, 1H). 13C NMR (100 MHz, CDCl3): delta 164.6, 158.9, 153.7, 146.5, 138.9, 136.5, 135.8, 129.8, 129.2, 129.1, 128.6, 128.5, 128.4, 128.1, 127.6, 127.5, 126.0, 125.9, 121.5, 117.4, 117.1, 114.4, 70.0, 69.9, 57.8. HRMS (ESI): Calcd for C25H21NO4Na: 422.1368. Found: 422.1349., 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
Article; Zhang, Qiang; Li, Jian-Feng; Tian, Guang-Hui; Zhang, Rong-Xia; Sun, Jin; Suo, Jin; Feng, Xin; Fang, Du; Jiang, Xiang-Rui; Shen, Jing-Shan; Tetrahedron Asymmetry; vol. 23; 8; (2012); p. 577 – 582;,
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

General procedure: To a solution of 15a (19.0 g, 107 mmol) in THF (300 mL) cooled to -78 ¡ãC was added n-butyllithium (47.2 mL, 118 mmol, 2.5 M solution in hexane) dropwise. The resulting solution was stirred at this temperature for 20 min before the dropwise addition of propionic anhydride (15.1 mL, 118 mmol). The cooling bath was removed, and the flask was allowed to slowly warm to room temperature and stir for an additional hour whereupon LCMS indicated reaction completion. The reaction was quenched with the addition of sat. NH4Cl. Volatiles were removed in vacuo, and the resulting residue was diluted with DCM. The layers were separated, and the organic layer was washed with water x 2, 1 M NaOH, brine, dried over MgSO4, filtered, and concentrated in vacuo to afford the desired product as a white solid (23.6 g, 94percent yield). Spectral data were in accordance with reported literature values.3, 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
Article; Reed, Carson W.; Fulton, Mark G.; Nance, Kellie D.; Lindsley, Craig W.; Tetrahedron Letters; vol. 60; 10; (2019); p. 743 – 745;,
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.

Production Example 1 (4R) -3- (4-Azidobutanoyl)4-phenyloxazolidin-2-one A catalytic amount of dimethylformamide was added to a solution of 4-azidobutyric acid (10.3 g, 80.0 mM) in 100 ml of methylene chloride and, thereafter, thionyl chloride (8.7 ml, 119.5 mM) was added dropwise thereto under ice-cooling. After stirring the reaction mixture at room temperature for one hour, it was evaporated to give a crude acid chloride. A 1.6M solution of n-butyl lithium in hexane (40.2 ml, 64.3 mM) was added dropwise into a solution of (4R)-4-phenyl-2-oxazolidinone (manufactured by Aldrich; 10 g, 61.3 mM) in tetrahydrofuran (80 ml) at -78¡ã C. and the mixture was stirred at the same temperature for 30 minutes. A solution of the previously synthesised acid chloride in tetrahydrofuran (100 ml) was slowly added dropwise into the reaction mixture and the mixture was further stirred for 30 minutes. The reaction was ceased by adding dropwise a saturated aqueous solution of sodium bicarbonate into the reaction mixture followed by warming up to room temperature. The mixture was poured into water followed by extracting with ethyl acetate and the organic layer was washed with a saturated aqueous solution of sodium bicarbonate, water and brine in this order and dried over anhydrous magnesium sulfate. The solvent was removed and the residue was subjected to a silica gel column chromatography (hexane/ethyl acetate=5/1) to give the title compound (17 g, 99percent). 1H-NMR(CD Cl3) delta:1.84(2H,quint,J=7 Hz), 2.88(2H,t,J=7 Hz), 3.25 (2H,t,J=7 Hz),4.24(1H,dd,J=4.9 Hz), 4.65(1H,t,J=7 Hz), 5.36(1H,dd,J=4.9 Hz), 7.22-7.35(5H,m)., 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; Eisai Co., Ltd.; US6218550; (2001); B1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem