Day: October 23, 2020

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 1; [0058] Synthesis of (4S)-4-phenyl-3-{[2-(trifluoromethyl)phenyllacetvU-l,3-oxazolin-2-one [Formula 35][0059]Triethylamine (51.5 mL, 368 mmol) was added to a suspension of 2- trifluoromethylphenylacetic acid (37.6 g, 184 mmol) and (s)-(+)-4-phenyl-2-oxazolidinone (15 g, 92 mmol) in toluene (450 mL) at room temperature. Pivaloyl chloride (22.7 mL, 184 mmol) was added dropwise to the suspension with stirring at room temperature. The resulting suspension was heated under reflux with stirring for 18 hours. After cooling to room temperature, 2 N hydrochloric acid (150 mL) was added, followed by extraction. The organic layer was sequentially washed with a saturated sodium bicarbonate solution (150 mL) twice, a 5% sodium chloride solution (150 mL) and water (150 mL) and concentrated under reduced pressure. Ethyl acetate (45 mL) was added to the resulting solid, and the solid was completely dissolved by heating to 5O0C. Heptane (180 mL) was added to the solution, followed by gradually cooling to room temperature. The resulting suspension was further cooled to ice-cold temperature, and then filtered, washed with heptane (150 mL) and dried under reduced pressure to obtain 27.7 g (content: 93%) of first crystals of the title compound. From the filtrate, 1.43 g (content: 87%) of second crystals were obtained. The crystals were combined to obtain the title compound as white crystals in a yield of 84%.1H-NMR (400 MHz, CDCl3): delta 4.34 (dd, J = 4.0, 8.8 Hz, IH), 4.47 (s, 2H), 4.76 (dd, J = 8.8, 9.2 Hz, IH), 5.44 (dd, J = 3.6, 8.8 Hz, IH), 7.21 (d, J = 7.6 Hz, IH), 7.26-7.40 (m, 6H), 7.46 (dd, J = 7.6, 7.6 Hz, IH), 7.62 (d, J = 8.0 Hz, IH)., 99395-88-7

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

Reference£º
Patent; Eisai R&;D Management CO., LTD.; UEMURA, Toshiyuki; SASAKI, Takeo; HOSHINO, Yorihisa; ISOMURA, Minetaka; WO2010/98496; (2010); 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.

Add 0.2 mmol of (R)-4-phenyl-2-oxazolidinone and a stirrer to a clean Schlenk reaction tube.Then, 1.0 mL of CH3CN solvent was added by a syringe, and 0.8 mmol of NaH was added to the reaction tube.Finally, 0.6 mmol of gem-dichloroarylethylene was added with a micro syringe, and the bottle was stoppered with a soft rubber stopper, and reacted at 100 ¡ã C for 23 hours.TLC dot plate detection; after the reaction is completed, the reaction solution is added with ice water and extracted with ethyl acetate three times.The organic layer is concentrated and separated by column chromatography to obtain pure (R)-4-phenyl-3-phenylethynyl-2-oxazolidinone.White solid, yield 83percent., 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; Jiangxi Normal University; Zhao Junfeng; Tu Yongliang; Zeng Xianzhu; (9 pag.)CN109320441; (2019); 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

Example-20: Preparation of (R)-4-phenyI-3-propionyIoxazolidin-2-one (Formula B-I) ( )-4-phenyloxazolidin-2-one (100 gm) and dimethylaminopyridine (10 gm) were added to a mixture of propionic acid (50 gm) and toluene (400 ml) at 25-30C. Cooled the reaction mixture to 0-5C, dicyclohexylcarbodiimide (151.5 gm) was slowly added and stirred the reaction mixture for 1 hr at the same temperature. Slowly raised the temperature of the reaction mixture to 25-30C and stirred for 14 hrs at the same temperature. Filtered the reaction mixture, aqueous hydrochloric acid solution was added to the filtrate and stirred the reaction mixture for 20 min at the same temperature. Both the organic and aqueous layers were separated and washed the organic layer with aqueous HC1 solution followed by with aqueous sodium bicarbonate solution and then with aqueous sodium chloride solution. Distilled off the solvent completely from the organic layer under reduced pressure and co- distilled with cyclohexane under reduced pressure. Cyclohexane (200 ml) was added to the obtained solid at 55-60C and stirred for 15 min at the same temperature. Cooled the reaction mixture to 25-30C and stirred for 40 min at the same temperature. Filtered the solid, washed with cyclohexane and dried to get the title compound. Yield: 124.0 gm. M.R: 81-82C., 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; MSN LABORATORIES PRIVATE LIMITED; THIRUMALAI RAJAN, Srinivasan; ESWARAIAH, Sajja; VENKAT REDDY, Ghojala; WO2015/87351; (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.875444-08-9,(4S,5R)-5-(3,5-Bis(trifluoromethyl)phenyl)-4-methyloxazolidin-2-one,as a common compound, the synthetic route is as follows.

875444-08-9, To a solution of (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyloxazolidin-2-one (1.84g, 5.89mmol) in DMF (10ml) was dropwise added NaHMDS (5.4ml, 5.4mmol) at – 40C. After being stirred for 30 min, the reaction mixture was slowly added with drops of a dilution of 2-chloro-3-(chloromethyl)pyrazine, obtained in step 2, in DMF (10ml). The resulting reaction mixture was warmed to room temperature, stirred for 3 hrs, diluted with ethyl acetate (200ml), and quenched with water (200ml). The organic layer was washed with water, dried over anhydrous magnesium sulfate, filtered, and concentrated in a vacuum. The residue was purified by chromatography to afford the title compound (900mg, 35%). H NMR (400MHz, CDCI3) 8.51 (d, 1 H), 8.36 (d, 1 H), 7.90 (s, 1 H), 7.83 (s, 2H), 5.85 (d, 1 H), 5.05 (d, 1 H), 4.50 (d, 1 H), 4.45 (m, 1 H), 0.81 (d, 3H).

The synthetic route of 875444-08-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; DONG-A ST CO.,LTD; PARK, Jang Hyun; SONG, Seung Hyun; CHUNG, Han Kook; KIM, Heung Jae; LEE, Ji Hye; JANG, Byeong Jun; KIM, Eun Jung; JUNG, Hae Hum; RYU, Chae Lim; HWANG, Jae-Sung; LEE, Hyung Ki; KANG, Kyung Koo; KIM, Soon Hoe; WO2014/157994; (2014); 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

To a suspension of (E)-3-(1 ,4-dimethyl-1 H-benzo[d][1 ,2,3]triazol-5-yl)acrylic acid (82 g, 376 mmol) in tetrahydrofuran (1 .5 L) was added triethylamine (131 ml_, 939 mmol). The reaction mixture was cooled to -25C and pivaloyl chloride (46 ml, 376 mmol) was added dropwise and stirred for 30 min at -25C. Lithium chloride (17.52 g, 413 mmol) was added in one- portion, followed by (S)-4-phenyloxazolidin-2-one (58.8 g, 361 mmol) and the reaction mixture was allowed to warm to room temperature and was stirred for 1 hr. The mixture was cooled to -25C and pivaloyl chloride (12ml, 98 mmol) was added dropwise and allowed to stir for an additional 1 hr. THF (300 mL) was added followed by (S)-4-phenyloxazolidin-2-one (10 g, 61 mmol) and pivaloyl chloride (18 ml, 147 mmol) and the mixture was stirred at 10C for 1 hr and then room temperature for 18 hr. The reaction mixture was diluted with ethyl acetate (1 L) and washed with 5% NaHS03(1 L). The resulting solid was collected by filtration and washed with water and diethyl ether to afford a light yellow solid (S,?)-3-(3-(1 ,4- dimethyl-1 H-benzo[c ][1 ,2,3]triazol-5-yl)acryloyl)-4-phenyloxazolidin-2-one (104.39 g, 288 mmol, 77 % yield). 1H NMR (DMSO-d6) delta: 8.05 (d, J=15.8 Hz, 1 H), 7.71 -7.88 (m, 3H), 7.30- 7.45 (m, 5H), 5.61 (m, 1 H), 4.83 (m, 1 H), 4.30 (s, 3H), 4.24 (m, 1 H), 2.78 (s, 3H). LC-MS: m/z 363.2 [M+H]+, 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; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; BROOKS, Carl A.; MATTHEWS, Jay M.; (59 pag.)WO2018/109646; (2018); 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.

Example 1: Preparation of ezetimibe; (1-1) Preparation of 3-[5-(fluorophenyl)-l,5-dioxapentyl]-4(S)- phenyl-2-oxazolidinone (Formula 7); 200 g of 5-(4-fluorophenyl)-5-oxopentanoic acid of formula 8, 16O g of (S)-4-phenyloxazolidine-2-one of formula 9, and 11.6 g of 4-dimethylaminopyridine were dissolved in 600 m? of dichloromethane to prepare a reaction mixture. A solution which was prepared by dissolving 157 g of N,N’-dicyclohexylcarboimide in 200 ml of dichloromethane was added to the reaction mixture and stirred for 2 hours. After completion of the reaction, the resulting reaction mixture was filtered to remove by-products. The filtrate thus obtained was washed successively with 1 I of 6N HCl, 1 ? of water, and 1 ? of saturated sodium chloride, dried over anhydrous magnesium sulfate, filtered, and distilled under a reduced pressure to remove the solvent. The residue thus obtained was dissolved in 2 I of methanol by heating and cooled to induce crystallization. 2 ? of water was added thereto and stirred for 30 min. The solid thus obtained was isolated by filtering to obtain 289 g of the title compound as a white solid (yield: 86%).1H NMR(300MHz, CDCl3) : delta 7.92 (2H, M), 7.35-7.13 (5H, m), 7.04 (2H, m), 5.43 (IH, q), 4.75(1H, t), 4.22 (IH, q), 3.05-2.93 (4H, m), 2.03 (2H, m), 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; HANMI PHARM. CO., LTD.; KIM, Gi Jeong; KIM, Choong Hahn; CHANG, Ji Yeon; KIM, Nam Du; CHANG, Young Kil; LEE, Gwan Sun; WO2010/71358; (2010); 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.

S-(+)-4-PHENYL-OXAZOLIDIN-2-ONE (2.81 g, 17.2 MMOL), 4-bromo-N-propyl- benzamide (4.17 g, 17.2 MMOL), CUL (0.32 g, 1.72 MMOL) and potassium carbonate (4.76 g, 17.2 MMOL) were charged to a nitrogen-purged flask. The flask was evacuated and backfilled with nitrogen before addition of dioxane (17.2 ml). To the above reaction mixture, 1, 2-diaminocyclohexane (0.21 ML, 1.72 MMOL) was added via syringe. The resulting bright blue mixture was heated at 110C FOR 15.5 hours. Analysis (HPLC/MS) of the reaction mixture indicated that the reaction was complete. The oil bath was cooled to 45C, and any precipitated product was dissolved by the addition of DICHLOROMETHANE (50 ml). The mixture was filtered through celite and the solids were washed with an additional 50 ml of warm dichloromethane. The combined filtrates were concentrated and vacuum dried to give the desired OXAZOLIDINE as a light brown solid in near quantitative yield (5.6 g). Mass spec: 325 (m +1). ‘H NMR (CDC13) 8 0.94 (t, J =7.5, 3H), 1.59 (m, 2H), 3.35 (m, 2H), 4.21 (m, 1 H), 4.80 (m, 1H), 5.43 (m, 1H), 6.16 (br, 1H), 7.27 (d, J=7.9, 2H), 7.34 (m, 3H), 7.46 (d, J =8.0, 2H), 7.64 (d, J =8.3, 2H). 3C NMR (CDC13) 8 11.66, 23. 08, 41.96, 60.54, 70.10, 120.10, 126,127. 95, 129.24, 129.75, 130.77, 137.96, 139.81, 155.84, 167. 02., 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; PFIZER PRODUCTS INC.; WO2004/39785; (2004); 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

Pent-4-enoic acid (1, 2.04 mL, 20 mmol) was dissolved in a DCM (dichloromethane) solvent (66 mL) and oxalyl chloride (2.03 mL, 24 mmol) was then added dropwise thereto. Subsequently, DMF (dimethylformamide) (200 muL) was added thereto, and the reaction was carried out at 40 C. for 1 hr. The reaction solution was cooled to room temperature and the solvent was removed therefrom using an evaporator. Subsequently, the resulting product was diluted with DCM (66 mL) and was then added dropwise to a solution of (S)-4-phenyloxazolidin-2-one (2, 3590 mg, 22 mmol), DIPEA (diisopropylethylamine) (6968 muL, 40 mmol), and DMAP (dimethylaminopyridine) (122.17 mg, 1 mmol) dissolved in DCM (36.6 mL). The resulting reaction solution was stirred at room temperature for 2 hr. After completion of the reaction, the reaction was terminated with 0.5 M HCl (50 mL), followed by extraction with DCM (60 mL, 20 mL¡Á3). The DCM layer was dried with anhydrous MgSO4 and then filtered. Further, column chromatography (ethyl acetate_hexane=1:2) was performed, thus yielding a desired compound (S)-3-(pent-4-enoyl)-4-phenyloxazolidin-2-one (3, 4219 mg, 86%). (S)-3-(pent-4-enoyl)-4-phenyloxazolidin-2-one (3) 4219 mg, 86%, White solid; Rf=0.5 (ethyl acetate_hexane=1:2); 1H NMR (400 MHz, CDCl3) delta 7.41-7.29 (m, 5H), 5.85-5.75 (m, 1H), 5.43 (dd, J=8.7 Hz, 3.6 Hz, 1H), 5.06-4.95 (m, 2H), 4.69 (t, J=8.8 Hz, 1H), 4.29 (dd, J=8.9 Hz, 3.64 Hz, 1H), 3.07-3.03 (m, 2H), 2.39-2.34 (m, 2H); 13C{1H} NMR (100 MHz, CDCl3) delta 172.2, 153.9, 139.2, 136.7, 129.3, 128.9, 126.1, 115.8, 70.2, 57.7, 35.0, 28.2; IR (KBr) 3069, 2979, 1780, 1706, 1385, 1326, 1200, 1060 cm-1; HRMS (EI) m/z: [M]+ Calcd for C14H15NO3 245.1052; Found 245.1051., 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; Kangwon National University, University Industry Cooperation Foundation; Lee, Phil Ho; Lee, Koo Yeon; Baek, Yonghyeon; Um, Kyusik; Kim, Byeong Su; (32 pag.)US2019/256479; (2019); 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

Step B: Preparation of (R.E)-4-phenyl-3-(3-(3A,5-trifluorophenyl)acryloyl)oxazolidin-2-one: A solution of (R)-4-phenyloxazolidin-2-one (3.92 g, 24.0 mmol) in THF (60 mL) was cooled to -78 C and lithium bis(trimethylsilyl)amide (25.2 mL, 25.2 mmol, 1.0 M in THF) was added dropwise over 10 minutes. The mixture was stirred at -78 C for 45 minutes and a solution of (E)-3-(3,4,5-trifluorophenyl)acryloyl chloride (5.56 g, 25.2 mmol) in THF (15 mL) was added. The mixture was stirred for 17 hours during which time the mixture reached ambient temperature and was poured into cold water (300 mE). The aqueous mixture was extracted with 50% EtOAc/hexanes (3 x) and the combined organic phases were washed with brine, dried over MgSO4lactivated carbon and filtered through a packed Si02 plug capped with a MgSO4 layer (50% EtOAc/hexanes for elution). The filtrate was concentrated in vacuo to afford (R, E)-4-phenyl-3 -(3-(3 ,4,5- trifluorophenyl)acryloyl)oxazolidin-2-one (8.40 g, 100%) as an ivory white solid. ?H NMR (CDC13) 7.84 (d, J 15.7 Hz, 1H), 7.57 (d, J 15.7 Hz, 1H), 7.42-7.33 (m, 5H), 7.21-7.18 (m, 2H), 5.54 (dd, J= 8.7, 3.9 Hz, 1H), 4.75 (t, J 8.8 Hz, 1H), 4.34 (dd, J 8.9, 3.9 Hz, 1H) ppm., 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; BRANDHUBER, Barbara, J.; KERCHER, Timothy; KOLAKOWSKI, Gabrielle, R.; WINSKI, Sharon, L.; WO2014/78323; (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.145589-03-3,(R)-4-Benzyl-3-(3-methylbutanoyl)oxazolidin-2-one,as a common compound, the synthetic route is as follows.

: Preparation of (S)-3-((S)-2-isopropylpent-4-enoyl)-4-benzyloxazolidin-2-one [Show Image] (a) Alkylation with allyl bromide: To a solution of lithium diisopropylamide (23 mL, 46 mmol; 2 M in THF) in anhydrous THF (120 mL), stirred at -78 C under argon, a solution of (S)-4-benzyl-3-(3-methylbutanoyl)oxazolidin-2-one (10.0 g, 38.27 mmol) in anhydrous THF (10 mL) was added and the mixture was stirred for 1.5 h. Then allyl bromide (16.22 g, 134.07 mmol) and DMPU (16 mL) were successively added dropwise. The resulting mixture was continued to stir at -78 C for 2 h and then allowed to reach -45 C at which it was stirred for 4 h. The mixture was allowed to warm to 10 C during 12 h. The reaction was quenched by the addition of saturated aqueous NH4Cl solution (100 mL) and the product was extracted with ethyl acetate (3 ¡Á 250 mL). The combined organic layers were successively washed with ice-cold HCl (1 M, 100 mL), saturated aqueous NaHCO3 solution (2 ¡Á 100 mL), and brine (2 ¡Á 100 mL), and then dried over anhydrous Na2SO4. After removal of the solvents under reduced pressure 14.46 g of crude product were obtained which were further purified by radial chromatography on silica gel (petrolether/ethyl acetate = 10:1) to afford 8.994 g (78 %) of alkylation product as a yellowish oil

145589-03-3, 145589-03-3 (R)-4-Benzyl-3-(3-methylbutanoyl)oxazolidin-2-one 11391340, aoxazolidine compound, is more and more widely used in various fields.

Reference£º
Patent; Krka Tovarna Zdravil, D.D., Novo Mesto; EP2189442; (2010); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem