Category: 99395-88-7

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 the soulution of compound 2 (700 g, 3.33 mol, 1.1 eq) dissolved in THF (5 L) was added triethylamine (1.2 L, 7.87 mol, 2.6 eq) at room temperature under N2 atmosphere. Then the solution of pivalic acid chloride (400 g, 3.33 mol, 1.1 eq) in THF (700 mL) was added dropwise to the reaction mixture cooled to -10 C for about 2 h. After addition, the mixture was stirred for 2 h at this temperature. TLC showed the compound 2 was consumed up, then the Evans auxiliary (493.5 g, 3 mol, 1 eq) and anhydrous LiCl (150.5 g, 3.5 mol,1.17 eq) were added sequencely. The mixture was warmed to room temperature and stirred for 2 h till the anhydride intermediate was consumed up. Then ethylacetate (2 L) and NH4Cl aq (1 L) were added, stirred for 15 min, stayed and separated, the aqueous layer was extracted with ethyl acetate (500 mL¡Á2), combined the organic phase, washed with water (250 mL ¡Á2), concentrated.The residue was recrystallized from isopropanol (7 L) to afforded compound 4 as a white solid (913.6 g, 85.0% yield). HPLC purity: 99.2%, mp: 94-95 C [lit.9(b) 91C]. 1H-NMR (CDCl3,400 MHz): delta 7.94-7.93 (m, 2H, J=2), 7.40-7.29 (m, 5H), 7.10-7.01 (m, 2H), 5.45-5.41 (m, 1H), 4.72-4.63 (m, 1H), 4.30-4.27 (m, 1H), 3.06 (t, 2H, J=8), 2.97 (t, 2H, J=12), 2.10-2.03 (m, 2H). 13C-NMR (CDCl3, 100MHz): delta 197.7, 172.2, 167.0, 164.4, 153.8, 139.2, 133.3, 130.7, 130.6, 129.2, 128.7, 126.0, 115.7, 115.5, 70.1, 57.6, 37.3, 34.8, 18.5. MS (ESI) m/z calcd. for C20H18FNO4: 355.12, calcd. for C20H18FNO4Na (M+Na)=378.12, found 378.04 (M+Na)., 99395-88-7

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

Reference£º
Article; Zhu, Yijun; Pan, Jing; Zhang, Shunli; Liu, Zhenren; Ye, Deyong; Zhou, Weicheng; Synthetic Communications; vol. 46; 20; (2016); p. 1687 – 1693;,
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

Step 1: To (S)-(+)-4-phenyl-2-oxazolidinone (9.88 g, 60 mmol) in THF (150 mL) at -78 C., was added n-butyl lithium (37.7 mL, 1.6M in hexanes, 60 mmol) over a period of 30 minutes. THF (50 mL) was added to the resultant thick suspension and the reaction mixture allowed to warm up to facilitate stirring. Trans-cinnamoylchloride (11.5 g, 69 mmol) in THF (30 mL) was added dropwise. The reaction was stirred at room temperature overnight. The reaction mixture was quenched with a saturated ammonium chloride solution (50 mL) and stirred for 0.5 h. The solvent was removed in vacuo, the residue dissolved in ethyl acetate, washed with water (300 mL), 5% sodium bicarbonate (200 mL) and brine (100 mL) and dried over sodium sulfate. The solvent was removed in vacuo to give a pale yellow solid. The compound was crystallized from ethylacetate and washed with hexanes to give 17.12 g (97%) of (S)-4-phenyl-3-[(E)-(3-phenyl-acryloyl)]-oxazolidin-2-one. 1H NMR (400 MHz, CDCl3): delta [ppm] 7.92 (d, 1H), 7.77 (d, 1H), 7.59 (m, 2H), 7.40-7.35 (m, 8H), 5.55 (dd, 1H), 4.74 (t, 1H), 4.31 (dd, 1H)., 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; Kong, Laval Chan Chun; Moinet, Christophe; Vaillancourt, Louis; Bubenik, Monica; US2006/14769; (2006); 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

INTERMEDIATE 45-({(2S, 5R)- 1 -(tert-butoxycarbonyl)-5-[(R)-hydroxy(phenyl)methyl]pyrroiidin-2- yl ) methyl)pyridine-2 -carboxylic acidStep A: (4)USD^-3-Hex-5-ynoyl-4-pheny – 1.3-oxazolidin-2-one; To a solution of 69.0 g (615 mmol) of 5-hexynoic acid and 214 mL (1540 mmol) of triethylamine in 1.0 L of anhydrous tetrahydrofuran at -25 C 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’~<4'3 " 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, 1H), 4.28 (dd, J= 9.2, 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

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

Reference£º
Patent; MERCK SHARP & DOHME CORP.; MORRIELLO, Gregori, J.; WENDT, Harvey, R.; EDMONDSON, Scott, D.; WO2012/12314; (2012); 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

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

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

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

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

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 4 PREPARATION OF 1-[(5-METHOXY-1,5-DIOXOPENTA)-YL1-4-(S)-PHENYL OXAZOLIDIN-2-ONE (FORMULA III) 300 g of monomethyl glutarate was taken into a four neck round bottom flask containing 1500 ml of dichloromethane under stirring. 684 ml of triethyl amine was added at 20 C. followed by the addition of 306 ml of pivaloyl chloride. The reaction mixture was stirred at room temperature for 3 hours. 267 g of (S)-4-Phenyl-2-oxazolidinone and 17 g of dimethyl aminopyrimidine was added and heated to 45 C. The reaction mass was maintained at 42 to 45 C. for 7 hours. Reaction completion was confirmed by thin layer chromatography. The reaction mass was cooled to room temperature and 1500 ml of water was added to it. The aqueous layer was separated and extracted with 750 ml of dichloromethane in two equal lots. Total organic layer was washed with 750 ml of water in two equal lots. The organic layer was evaporated under vacuum at 63 C. to get an oily compound. 1200 ml of n-heptane was charged to this oily compound and stirred for 60 minutes. Filtered the separated solid and washed with 600 ml of n-heptane. The compound was dried at 30 C. for 8 hours to get 449 g of the title compound as a crystalline solid. (Yield 75%) Purity by HPLC: 93.48%., 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; Uppala, Venkata Bhaskara Rao; Vaddadi, Pattabhi Ramayya; Sunkara, Vishnu Vardhan; Cheemalapati, Venkata Annapurna Sasikala; Padaga, Kanaka Seshu Kumar; US2007/49748; (2007); 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.

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