Heterocyclic Building Blocks-Oxazolidine

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

145589-03-3, (R)-4-Benzyl-3-(3-methylbutanoyl)oxazolidin-2-one is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Eine Loesung von 290 g 4S-Benzyl-3-(3-methyl-butyryl)-oxazolidin-2-one in 0,58 l Tetrahydrofuran wird auf -78 C gekuehlt und waehrend 65 Minuten 1,14 l 1 M Lithiumhexamethyldisilazid (in Tetrahydrofuran) zugetropft. Das Gemisch wird noch 1 Stunde bei -78 C nachgeruehrt und anschliessend mit der vorbereiteten Loesung von trans-1-Chloro-3-iod-propen in Tetrahydrofuran versetzt. Man laesst die Temperatur auf 0 C steigen und ruehrt noch weitere 20 Stunden nach. Das Reaktionsgemisch wird mit 500 ml 10%-iger Ammoniumchloridloesung versetzt und mit Diethylether extrahiert (2x 1 l). Die organischen Phasen werden mit Wasser (1x 1 l) gewaschen, mit Natriumsulfat getrocknet und eingedampft. Aus dem Rueckstand wird mittels Flashchromatographie (SiO2 60F / Essigsaeureethylester/Hexan 5:1) die Titelverbindung B3 als leicht oranges Oel erhalten (582 g, 78 %). 1H-NMR (400 MHz, CDCl3, delta) : 0,85 (m, 6H), 2,02(m, 1H), 2,3 – 2,55 (m, 2H), 2,75 (m, 1H), 3,30 (m, 1H), 3,88 (m, 1H), 4,18 (m, 2H), 4,70 (m, 1H), 5,80 – 6,10 (m, 2H), 7,15 – 7,40 (m, 5H) ppm. Herstellung von trans- 1-Chlor-3-iod-propen: Eine Loesung von 184,7 g trans-1,3-Dichlorpropen in 0,58 l Tetrahydrofuran wird mit 266,1 g Natriumiodid versetzt und unter Lichtausschluss waehrend 30 Minuten bei Raumtemperatur geruehrt. Das Gemisch wird klarfiltriert und das Filtrat direkt eingesetzt., 145589-03-3

As the paragraph descriping shows that 145589-03-3 is playing an increasingly important role.

Reference£º
Patent; Speedel Pharma AG; EP1200384; (2004); B1;,
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

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

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

108149-60-6, (S)-(-)-3-tert-Butoxycarbonyl-4-methoxycarbonyl-2,2-dimethyl-1,3-oxazolidine is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To an ice cold solution of commercially available 1 (35 g, 135 mmol) in THF/MeOH (500 mL (95:5)), was added LiBH4 (5.9 g, 271 mmol) portionwise and the suspension was stirred for 2 h at RT. The reaction mixture was cooled and quenched with ice. Solvent was removed under reduced pressure, and water was added. The aqueous layer was extracted with EtOAc, concentrated and chromatographed (EtOAc:hexanes, 3:7) to yield 2 (23 g, 74 % yield)., 108149-60-6

As the paragraph descriping shows that 108149-60-6 is playing an increasingly important role.

Reference£º
Patent; EXELIXIS, INC.; XU, Wei; (170 pag.)WO2017/4609; (2017); 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

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