Category: 90319-52-1

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 the solution of (?)-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 N2 atmosphere and cooled to – lOoC (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 – lOoC 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 N2 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

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

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.90319-52-1,(R)-4-Phenyloxazolidin-2-one,as a common compound, the synthetic route is as follows.

To a solution of Preparation 4H (1.4 g, 4.8 mmol) in THF (15 mL) was added NEt3 (1.3 mL, 9.6 mmol). The reaction mixture was cooled to 0 ¡ãC and trimethylacetyl chloride (0.7 13 mL, 5.8 mmol) was added dropwise and the resulting solution stirred for 30 mm at 0 ¡ãC. In a separate flask, (R)-4-phenyloxazolidin-2-one (3, 1.01 g, 6.24 mmol) in THF (45 mL) at 0 ¡ãC was treated with 1 M LiHMDS solution in THF (dropwise addition of 6.24 mL, 6.24 mmol) and stirred at 0¡ãC. The lithiate was added via cannula to the first flask. The reaction mixture was allowed to warm to rt and was stirred for 3 hours. LC/MS indicated the complete consumption of the starting carboxylic acid and formation of the desired imide. The reaction mixture was poured onto saturated aqueous ammonium chloride (50 mL) and the layers were separated. The aqueous layer was extracted with EtOAc (3 x 50 mL). The combined organic extracts were dried over anhydrous sodium sulfate and chromatographed on silica using EtOAc/Hexanes 0 to 100percent 0 + 1gradient to give Preparation 41 as a white foam in 83/0 yield. m/z (M+H) = 433.3. H-NMR (400MHz; CDC13): oe 8.80 (d, J= 4.5 Hz, 1H), 8.11 (dd, J= 9.1, 5.7 Hz, 1H), 7.63 (dd, J 10.5, 2.5Hz, 1H), 7.48-7.43 (m, 1H), 7.40-7.30 (m, 6H), 5.47-5.44 (m, 1H), 4.71 (t, J 8.9 Hz, 1H), 4.31-4.28 (m, 1H), 3.20-3.11 (m, 3H), 2.49-2.46 (m, 1H), 1.82-1.67 (m, 6H)., 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; BRISTOL-MYERS SQUIBB COMPANY; CHERNEY, Emily, Charlotte; SHAN, Weifang; ZHANG, Liping; WILLIAMS, David, K.; GUO, Weiwei; HUANG, Audris; BALOG, James, Aaron; (72 pag.)WO2017/192844; (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.90319-52-1,(R)-4-Phenyloxazolidin-2-one,as a common compound, the synthetic route is as follows.

A solution of methyl fumarate (8) (2.66 g, 20.4 mmol) and pivaloyl chloride (2.70 g, 2.76 mL, 22.5 mmol) in THF (40 mL) was cooled to ?20 ¡ãC.? Triethylamine (4.13 g, 5.68 mL, 40.8 mmol) was added dropwise, and the mixture was stirred 1.5 h at ?20 ¡ãC.? The cooling bath was removed, and the solution was allowed to warm to room temperature.? Solid LiCl (0.953 g, 22.5 mmol) and (R)-phenyl-oxazolidone 9 (5.00 g, 30.6 mmol) were added portionwise, and the reaction was stirred 12 h. H2O (10 mL) and ethyl acetate (50 mL) were added. The layers were separated, and the aqueous layer was extracted with ethyl acetate (2 x 10 mL).? The combined organic layers were washed with 1 M HCl (1 x 25 mL), saturated Na2CO3 (2 x 50 mL), saturated brine (1 x 50 mL), dried (Na2SO4), and concentrated under reduced pressure.? The crude product was purified by flash chromatography, eluting with hexanes/ethyl acetate (3:1) to provide 4.38 g (78percent) of the chiral methyl fumarate 7 as a white solid: mp 92-94 ¡ãC; 1H NMR (400 MHz) delta 8.17 (d, J = 15.7 Hz, 1 H), 7.43 (comp, 5 H), 6.87 (d, J = 15.7, 1 H), 5.50 (dd, J = 4.0, 8.9 Hz, 1 H), 4.76 (t, J = 8.9 Hz, 1 H), 4.36 (dd, J = 4.0, 8.9 Hz, 1 H), 3.81 (s, 3 H); 13C NMR (100 MHz) delta 165.1, 163.1, 153.2, 138.2, 133.8, 132.2, 129.1, 128.8, 125.9, 70.2, 57.7, 52.2; IR (neat) 1780, 1727, 1690, 1387, 1341, 1306, 1279, 1196 cm-1; mass spectrum (CI) m/z 275.0869 [C14H13NO5 (M+1) requires 275.0794]., 90319-52-1

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

Reference£º
Article; Hethcox, J. Caleb; Shanahan, Charles S.; Martin, Stephen F.; Tetrahedron Letters; vol. 54; 16; (2013); p. 2074 – 2076;,
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

Preparation of (i?,E)-3-(3-(3,5-difluorophenyl)acryloyl)-4-phenyloxazolidin-2-one: To a solution of (E)-3-(3,5-difluorophenyl)acrylic acid (10.0 g, 54.3 mmol) in Et20 (150 mL) at 0 ¡ãC was added DIEA (9.48 mL, 54.3 mmol) followed by pivaloyl chloride (6.69 mL, 54.3 mmol). The mixture was stirred at 0 ¡ãC for 1 hour and cooled to – 78 ¡ãC. Meanwhile (R)-4- phenyloxazolidin-2-one (8.86 g, 54.3 mmol) in THF (200 mL) was cooled to -78 ¡ãC and butyllithium (21.7 mL, 2.5 M, 54.3 mmol) was added slowly. The mixture was stirred for 20 minutes at -78 ¡ãC and transferred by cannula to the solution of mixed anhydride. The combined mixture was stirred at -78 ¡ãC for 15 min, allowed to warm to 0 ¡ãC and stirred for an additional 30 minutes. The reaction mixture was quenched with saturated NH4C1 (25 mL), diluted with EtOAc (600 mL), washed with water, NaHC03, and brine, dried over MgSC^, and concentrated in vacuo. The crude material was purified by silica column chromatography, eluting with 10-20percent Ethyl acetate/Hexanes to afford the product (11.0 g, 61.5percent yield)., 90319-52-1

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

Reference£º
Patent; ARRAY BIOPHARMA INC.; ALLEN, Shelley; ANDREWS, Steven, W.; BLAKE, James, F.; CONDROSKI, Kevin, R.; HAAS, Julia; HUANG, Lily; JIANG, Yutong; KERCHER, Timothy; KOLAKOWSKI, Gabrielle R.; SEO, Jeongbeob; WO2012/158413; (2012); 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.90319-52-1,(R)-4-Phenyloxazolidin-2-one,as a common compound, the synthetic route is as follows.

(R) -4-phenyl-2-oxazolidinone (16.3 g,1 eq.) Was dissolved in 180 ml of dichloromethane,A mixture of triethylamine (15.2 g, 1.5 equiv) was added with stirring at 0 ¡ã C,4-dimethylaminopyridine (DMAP) (366 mg, 0.03 equiv)Subsequently, propionyl chloride (9.2 g, 1 equivalent) was added dropwise, and the mixture was stirred at 0 ¡ã C for 1 hour,Add methylene chloride diluted, washed with water, saturated sodium bicarbonate,The organic phase was dried over anhydrous sodium sulfate. The solvent was removed by evaporation under reduced pressure,Get the crude product. The crude product was purified by column chromatography,To give the title compound (III-a) (20.1 g, yield 92percent).

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

Reference£º
Patent; Zhejiang Yongning Pharmaceutical Co., Ltd.; Ye Tianjian; Lu Xiuwei; Yu Guangliang; Liu Ting; (14 pag.)CN105085322; (2017); B;,
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

[003491 Step A: Preparation of (R)-3-cinnamoyl-4-phenyloxazolidin-2-one: A THF (50 mE) solution of (R)-4-phenyloxazolidin-2-one (5.90 g, 36.2 mmol) was cooled to -78 ¡ãC and treated with lithium bis(trimethylsilyl)amide (36.9 mL, 36.9 mmol, 1.0 M in THF) dropwise. over 15 minutes. After 15-minute stirring at -78 ¡ãC, a THF (10 mE) solution of cinnamoyl chloride (6.33 g, 38.0 mmol) was introduced. The mixture was stirred for 1 hour at -78 ¡ãC and 2 hours at ambient temperature before it was quenched with saturated NaHCO3 (50 mL) and stirred for 1 hour. The mixture was diluted with EtOAc (200 mL), washed with water and brine, dried over MgSO4, filtered and concentrated to give the product as a pale yellow solid (10.6 g, 99.9percent yield). MS (apci) mlz = 293.9 (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; ARRAY BIOPHARMA INC.; ALLEN, Shelley; ANDREWS, Steven Wade; BLAKE, James F.; BRANDHUBER, Barbara J.; JIANG, Yutong; KERCHER, Timothy; WINSKI, Shannon L.; WO2014/78372; (2014); 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.

Example 11 (R,E)-3-(3-(3-methoxy)phenyl)acryloyl)-4-phenyl oxazolidin-2-one The 4R-phenyl-2-oxazolidinone (5.6 g, 34.4 mmol) was placed in a three-necked flask, after it was purged with nitrogen, tetrahydrofuran was added and it was cooled to -78¡ã C., then n-butyl lithium (1.6M, 22 ml, 35.4 mmol) was added dropwise, and the reaction was carried out for 30 minutes. After a solution of m-methoxy cinnamoyl chloride (10.3 g, 37.8 mmol) in tetrahydrofuran was added dropwise, the reaction was continued for 30 minutes, then it was slowly raised to 0¡ã C., the reaction was continued for 2 hours and quenched with saturated ammonium chloride solution. The mixture was concentrated to remove tetrahydrofuran and extracted with ethyl acetate 3 times, then the organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, concentrated, and recrystallized with petroleum ether and ethyl acetate to give a white solid 10.3 g, yield: 92percent. 1HNMR (300 MHz, CDCl3): delta 8.0 (1H, d, J=15.3), 7.8 (1H, d, J=15.7), 7.2-7.4 (6H, m), 7.1-7.2 (2H, m), 7.0 (1H, d, J=8.6), 5.6 (1H, dd, J=4.0, 9.0), 4.8 (1H, t, J=8.8, 17.5), 4.3 (1H, dd, J=4.0, 8.8), 3.8 (3H, s). ESI-MS: 346.3 (M+Na)., 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; Zhang, Qiang; Zhang, Rongxia; Tian, Guanghui; Li, Jianfeng; Zhu, Fuqiang; Jiang, Xiangrui; Shen, Jingshan; US2014/46074; (2014); 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.

(R) -4-phenyl-2-oxazolidinone (16.3 g,1 eq.) Was dissolved in 180 ml of dichloromethane,A mixture of triethylamine (15.2 g, 1.5 equiv) was added with stirring at 0 C,4-dimethylaminopyridine (DMAP) (366 mg, 0.03 equiv)Subsequently, propionyl chloride (9.2 g, 1 equivalent) was added dropwise, and the mixture was stirred at 0 C for 1 hour,Add methylene chloride diluted, washed with water, saturated sodium bicarbonate,The organic phase was dried over anhydrous sodium sulfate. The solvent was removed by evaporation under reduced pressure,Get the crude product. The crude product was purified by column chromatography,To give the title compound (III-a) (20.1 g, yield 92%).

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; Zhejiang Yongning Pharmaceutical Co., Ltd.; Ye Tianjian; Lu Xiuwei; Yu Guangliang; Liu Ting; (14 pag.)CN105085322; (2017); B;,
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.

Example 24 3-[(3R)-1-oxo-3-[3-(phenylmethoxy)phenyl]pentyl]-4R-phenyl-2-Oxazolidinone The 4R-phenyl-2-oxazolidinone (3.5 g, 21.4 mmol) was placed in a three-necked flask, after it was purged with nitrogen, tetrahydrofuran was added and it was cooled to -78¡ã C., then n-butyl lithium (1.6M, 13.8 ml, 22 mmol) was added dropwise, and the reaction was carried out for 30 minutes. After that, a solution of (R)-3-(3-(benzyloxy)phenyl)pentanoyl chloride (7.1 g, 23.6 mmol) in tetrahydrofuran was added dropwise, the reaction was continued for 30 minutes, then it was slowly raised to 0¡ã C., the reaction was continued for 2 hours, and then quenched with saturated ammonium chloride solution. The reaction solution was then concentrated to remove tetrahydrofuran and extracted with ethyl acetate 3 times, then the organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, concentrated, and recrystallized with petroleum ether and ethyl acetate to give a white solid 8.6 g, yield: 85percent. 1HNMR (CDCl3): delta 7.3-7.5 (8H, m), 7.1-7.2 (3H, m), 6.7-6.9 (3H, m), 5.2 (1H, dd, J=3.7, 8.6), 5.1 (2H, s), 4.5 (1H, t, J=8.9, 17.1), 4.2 (1H, dd, J=3.5, 8.6), 3.5 (1H, dd, J=8.9, 16.4), 3.2 (1H, d, J=5.6), 3.1 (1H, m), 1.5-1.7 (2H, m), 0.9 (3H, t, J=7.3, 14.7). ESI-MS: 430.5 (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; Zhang, Qiang; Zhang, Rongxia; Tian, Guanghui; Li, Jianfeng; Zhu, Fuqiang; Jiang, Xiangrui; Shen, Jingshan; US2014/46074; (2014); 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.

A reactor was charged with THF (1138 kg) and 2-((ls,4s)-4-(6-fluoroquinolin- 4-yl)cyclohexyl)acetic acid (105.1 kg, 1.0 equiv). The mixture was cooled to -5 to 5 C. Pivaloyl chloride (64.0 kg, 1.45 equiv) was charged. Triethylamine (101.1 kg, 2.70 equiv) was charged, maintaining temperature -5 to 5 C, then the mixture was aged 1 h. (i?)-(-)-4-Phenyl-2- oxazolidinone (68.1 kg, 1.15 equiv) and lithium chloride (20.2 kg, 1.30 equiv) were charged then the reactor wall was rinsed with THF (15.8 kg). The mixture was warmed to 25 C and held for 8 h. Water (1050.6 kg) and isopropyl acetate (825.8 kg) were added into the mixture. After mixing for 1 h, the phases were allowed to separate and the bottom aqueous layer was discarded. The organic stream was then washed with 10 wt% aqueous NaCl (1050 kg). The organic stream was concentrated until 500 L left. Isopropyl acetate (466.3kg) was added, and the organic stream was concentrated until 500 L left. Isopropyl acetate (1850.5 kg) was added into the mixture at 45-55 C and stirred for 1 h. The organic stream was filtered to remove inorganics and the filter was rinsed with isopropyl acetate (187.0 kg). The combined stream was concentrated under reduced pressure until 700 L was left. [00236] The organic stream was heated to 70-75 C until the solid completely dissolved. The mixture was cooled to 45 C then seeds (0.2 kg) were added into the mixture. The mixture was stirred for 1 h. ^-Heptane (1178.5 kg) was added into the mixture over 3 hours, then aged at 45 C for lh. The mixture was cooled to 10 C over 4 hours, and allowed to age for 6 hours. The slurry was filtered with a centrifuge. The solid was rinsed with a pre-mixed solution of isopropyl acetate (45.2 kg) and ^-heptane (321.5 kg). The solids were then rinsed with ft-heptane (2 x 358.2 kg). The cake was dried under vacuum at <50C to obtain 139.6 kg product in 88.2% yield, 99.95 HPLC area percent as a white solid. NMR (600 MHz, DMSO-de) 5 8.80 (d, J = 4.5 Hz, 1H), 8.08 (dd, J = 9.2, 5.8 Hz, 1H), 7.92 (dd, J = 10.9, 2.6 Hz, 1H), 7.63 (td, J = 8.7, 2.6 Hz, 1H), 7.43 (d, J = 4.5 Hz, 1H), 7.39-7.35 (m, 2H), 7.34-7.27 (m, 3H), 5.50 (dd, J = 8.7, 3.8 Hz, 1H), 4.75 (t, J = 8.7 Hz, 1H), 4.16 (dd, J= 8.7, 3.8 Hz, 1H), 3.34-3.25 (m, 1H), 3.17 (dd, J = 15.6, 6.8 Hz, 1H), 3.02 (dd, J = 15.7, 8.0 Hz, 1H), 2.35 (br s, 1H), 1.83-1.75 (m, 2H), 1.73-1.56 (m, 6H); 13C NMR (150 MHz, DMSO-de) d 171.6, 160.7, 159.1, 153.7, 152.2, 152.1, 149.8, 145.1, 140.0, 132.6, 132.6, 128.7, 127.9, 127.1, 127.1, 125.7, 119.0, 118.8, 118.4, 107.1, 107.0, 69.9, 57.0, 37.4, 36.5, 29.6, 29.0, 28.7, 27.4. HRMS (ESI) calculated for C26H26FN2O3 [M + H]+: 433.1922, found 433.1936., 90319-52-1

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

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; DELMONTE, Albert, J.; COHEN, Benjamin, M.; FRAUNHOFFER, Kenneth, Joseph; KOLOTUCHIN, Sergei; GONZALEZ-BOBES, Francisco; BEUTNER, Gregory, Louis; FREITAG, Adam, Joseph; BULTMAN, Michael, Scott; FAN, Yu; MAITY, Prantik; YOUNG, Ian, Scott; BECK, Hilary, Plake; OSPOV, Maksim; POWERS, Jay, Patrick; REILLY, Maureen, Kay; SHUNATONA, Hunter, Paul; WALKER, James, Ross; ZIBINSKY, Mikhail; (75 pag.)WO2019/6292; (2019); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem