Month: October 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

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

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

Example 21 (S,E)-3-(pent-2-enoyl)-4-phenyl oxazolidin-2-one The 4S-phenyl-2-oxazolidinone (5.6g, 34.4mmol) was placed in a three-necked flask, after it was purged with nitrogen, tetrahydrofuran was added and it was cooled to -78C, then n-butyl lithium (1.6M, 22ml, 35.4mmol) was added dropwise, and the reaction was carried out for 30 minutes. After that, a solution of 2-pentenoyl chloride (4.2g, 35.5mmol) in tetrahydrofuran was added dropwise, and the reaction was continued for 30 minutes, then it was slowly raised to 0C, the reaction was continued for 2 hours and 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 8g, yield: 95%. 1HNMR(300MHz, CDCl3): delta 7.3-7.4(5H, m), 7.1-7.2(1H, m), 6.9-7.1(1H, m), 5.5(1H, dd, J=4.2,19.0), 4.8(1H, t, J=9.6, 18.7), 4.2(1H, dd, J=3.7,18.9), 2.2(2H, m), 1.0(3H, t, J=7.4,14.9). ESI-MS: 246.4(M+H)., 99395-88-7

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

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

5-(4-Fluorophenyl)-5-oxopentanoic acid (21.02 g, 100.0 mmol) and 4 dimethylamino- pyridine (16.25 g, 133.0 mmol) were dissolved in N,N-dimethylformamide (100 mL, 1.0 M) to afford a copious white precipitate suspended in solution. The reaction was cooled to 2 0C (ice/water bath), and trimethylacetyl chloride (16.40 mL, 16.04 g, 133.0 mmol) was added drop-wise to afford a pale yellow mixture. The rate of addition was controlled in order to keep the temperature at or below 5 0C. A heavy white precipitate was formed and the mixture was allowed to warm to room temperature and stirred for 1.5 h. The mixture was charged with (6)-(+)-4-phenyl-2- oxazolidinone (16.32 g, 100.0 mmol) and 4-dimethylaminopyridine (12.22 g, 100.0 mmol) both as solids to afford a yellow colored suspension. The reaction was stirred at 30 C – 35 0C for 2 h. An aliquot was removed for analysis by TLC and HPLC. The pale olive colored suspension was poured into water (400 mL) while stirring vigorously and cooling the mixture in an ice-brine bath, transferred with water (150 mL) and stirred with ice-cooling for 1.5 h to afford a solution with an off-white precipitate. The compound was filtered, transferred with water (2 x 25 mL), washed with water (50 mL) and air dried for 15 min to afford an off-white moist clumpy powder. The material was crystallized from isopropanol (58.0 mL; 1.6 mL/g theoretical yield) by heating to near reflux to afford a golden yellow colored solution. The solution was cooled slowly to room temperature over 12 h, a seed crystal was added and crystals began to precipitate. The mixture was cooled in an ice/water bath and stirred for 1 h. The crystals were filtered, transferred with cold isopropanol (2 x 10 mL), washed with cold isopropanol (25 mL), air dried and vacuum dried to constant weight to afford (45)-4-phenyl-3-[5-(4-fluorophenyl)-5-oxopentanoyl]-l,3- oxazolidin-2-one (30.46 g, 85.7 % yield) as a white crystalline solid; m.p. 91.0 0C; EPO R/ 0.40 (1:2 ethyl acetate-hexane); HPLC Rr7.02 min; HPLC purity 94 %. 1H NMR (300 MHz, CDCl3) delta 7.93 (dd, J= 5.4, 9.0 Hz, 2H), 7.28-7.42 (m, 5H), 7.10 (dd, J= 8.5, 9.0 Hz, 2H), 5.43 (dd, J= 3.7, 8.7 Hz, IH), 4.70 (t, J= 8.9 Hz, IH), 4.28 (dd, J= 3.7, 8.7 Hz, IH), 3.05 (dt, J= 1.2, 7.3 Hz, 2H), 2.97 (t, J= 7.3, 2H), 2.05 (p, J= 7.3 Hz, 2H), ppm., 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; MICROBIA, INC.; WO2006/122216; (2006); A2;,
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

Compound I (21 g, 0.1 mol) was added to a 500 ml three-necked flask, Triethylamine 20 ml and dichloromethane 250 ml, Stuttgart dropwise pivaloyl chloride (14.4g, 0.12mol), (4S) -4-phenyl-2-oxazolidinone (24.5 g, 0.15 mol), DMF 5 ml, 4,4-dimethylaminopyridine (1.22 g, 0.01 mol) was added after refluxing for 3 h, After refluxing for 10 h, Ice bath cooling, Then, 200 ml of 5 M hydrochloric acid was added dropwise at 0 C, Static stratification, The lower methylene chloride layer was washed successively with saturated sodium bicarbonate solution and water, Dried over anhydrous sodium sulfate. The filtrate was concentrated to dryness, To give 24.9 g of a white solid compound II, Yield 70%., 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; Suzhou Puluoda Biological Science and Technology Co., Ltd.; Luo, Ruixue; (14 pag.)CN106397292; (2017); A;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

695-53-4,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.695-53-4,5,5-Dimethyloxazolidine-2,4-dione,as a common compound, the synthetic route is as follows.

To 14 g of Exemplified compound (12B) in 150 ml of methylene chloride solution, 3.2 g of bromine in 20 ml of methylene chloride solution was added dropwise, while the mixture was cooled on ice. After stirring was continued at room temperature for 30 minutes, water was added to the resulting mixture. The aqueous phase was separated. The organic phase was dried with magnesium sulfate anhydride, and then condensed by vacuum distillation. 20 ml of N,N-dimethylacetoamide was added to the residue. The resulting liquid was added dropwise to 7.7 g of 5,5-dimethyloxazolidine-2,4-dione and 8.3 ml of triethylamine in 100 ml of N,N-dimethylacetoamide solution, while the mixture was cooled on ice. Then, the mixture was stirred at room temperature for 2 hours. Ethyl acetate and water were added to the reaction mixture. The aqueous phase was separated. The organic phase was washed with 1N-aqueous solution of potassium carbonate and 1N-aqueous hydrochloric acid solution and saturated brine. The organic phase was dried with magnesium sulfate anhydride, and then condensed by vacuum distillation. The residue was crystallized from a mixed solvent of ethyl acetate and hexane to obtain 14 g of Exemplified compound (16B).

The synthetic route of 695-53-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; FUJIFILM Corporation; US7365199; (2008); B2;,
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

In a 500 ml three-necked flask, 20 g (0.122 mol, leq.) Of the (s) -4-phenyl-2-oxazolone raw material and tolueneWas cooled to between 0 and 10 C, and 22 g (0.146 piomicron1, 1.2 eq.) Of t-butyldimethylchlorosilane was added and maintained at 0 toL0 C for 30 minutes under stirring, diisopropylethylamine 19.6g (0.152mall, 1.25eq.), Dropping the process to control the material temperatureAfter 0-10 C, the mixture was stirred at 0-10 C for 2 hours until the (S) -4-phenyl-2-oxazolone was subjected to TLCThe reaction was completed (TLC conditions: petroleum ether / ethyl acetate = 2/1). Then 36.7 g monoethyl malonate chloride was added(0.244piomicron1,2 eq.), Dropping process control the material temperature between 0 ~ 10 C, after the completion of the drop by adding 0.32g anhydrous fourButyl ammonium fluoride (TBAF, 1.2 O1, O. Oleq.) Was added and the reaction was stirred at room temperature for 2-5 hours. After completion of the reaction, the reaction solution was addedPoured into 200 ml of ice water and stirred at room temperature for 30 minutes. The organic phase was separated and the organic phase was washed with 10% sodium carbonate solution,The organic phase was evaporated to dryness to give a crude product. To the crude product isopropyl alcohol l0ml, stirring at 10 ~ 15 C 2 small, And dried to obtain 31.4 g of a product compound in a yield of 93%., 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; Zhangjiagang Hengsheng Pharmaceutical Co Ltd; Ding, Zunliang; Wang, Xilin; Wu, Haufeng; Zhang, Qingyun; (15 pag.)CN105524010; (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.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

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.

In anhydrous and oxygen-free environment, 36g of 4-[2-(4-fluoro-phenyl)-[1,3]dithiacyclolan-2-yl]-butyric acid (IV) was added and 300ml of dichloromethane was added. Add 50ml triethylamine,A mixture of 20 ml of pivaloyl chloride and 50 ml of tetrahydrofuran was added dropwise at a temperature of -20C to -10C and reacted for 2 hours. Add 6.4g of anhydrous lithium chloride and stir for 2 hours.27g 4-phenyl-2-oxazolidone was added and the reaction mixture was stirred for 5-7 h, extracted,Crystalline Intermediate VI, yield 96.1%., 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; Shandong New Age Pharmaceutical Co., Ltd.; Zhang Guimin; Zang Chao; Xia Mingjun; (15 pag.)CN107488138; (2017); 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.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.99395-88-7,(S)-4-Phenyloxazolidin-2-one,as a common compound, the synthetic route is as follows.

To a solution of (4S)-phenyl-2-oxazolidinone (400 mg, 2.45 mmol) in DMF (5 mL) at 0 C. was added NaH (60% in mineral oil, 117 mg, 2.94 mmol), and the reaction mixture was stirred for 5 min. Benzyl-2-bromoacetate (737 muL, 4.65 mmol) was added and the reaction mixture was stirred at 23 C. for 17 h. The reaction mixture was partitioned between 1.0 N HCl (100 mL) and ethyl acetate (200 mL). The organic layer was washed with saturated aqueous NaHCO3 (100 mL), brine (100 mL), dried over Na2SO4, and concentrated in vacuo to yield a brown oil that was purified by silica gel column chromatography (0-50% EtOAc in hexanes) to yield (2-oxo-[4S]-phenyloxazolidin-3-yl) acetic acid benzyl ester (635 mg, 83%)., 99395-88-7

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

Reference£º
Patent; VICURON PHARMACEUTICALS INC.; US2006/211603; (2006); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem