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

To a solution of (S)-4-phenyloxazolidin-2-one (0.737 g, 4.517 mmol) in DMF was added sodium hydride (0.189 g, 4.73 mmol) and the reaction stirred at ambient temperature for 45 minutes. 3-Bromo-5-chloropyrazolo[l,5-a]pyrimidine (1.00 g, 4.302 mmol) was added and the reaction stirred at ambient temperature for 3 hours. The reaction mixture was poured into water and the water layer extracted with ether. The combined organic layers were washed with brine, dried over MgSC^ and concentrated in vacuo. The crude material was purified by normal phase chromatography using 2% EtOAc/DCM as the eluent to yield (S)-3-(3-bromopyrazolo[l,5-a]pyrimidin-5-yl)-4-phenyloxazolidin-2-one (1.233 g, 3.433 mmol, 79.80 % yield)., 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; ARRAY BIOPHARMA INC.; ANDREWS, Steven W.; CONDROSKI, Kevin Ronald; DE MEESE, Lisa A.; FELL, Jay Bradford; FISCHER, John P.; LE HUEROU, Yvan; JOSEY, John A.; KOCH, Kevin; MIKNIS, Gregory F.; RODRIGUEZ, Martha E.; TOPALOV, George T.; WALLACE, Eli M.; XU, Rui; WO2011/29027; (2011); 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.

4-Pentenoic acid (compound X), 4-dimethylammoniumpyridine (DMAP) was added to a mixture of methylene dichloride and DMF at about 20C to about 30C and the reaction mass was cooled to about 15C to about 20C. Triethylamine and (S)-(+)-4-Phenyl-2-oxazolidinone (compound GammaChi’) was added to the reaction mass and the reaction mass was stirred for about 5-10 minutes. The reaction mass was then cooled to about 0C to about 5C. A solution of pivaloyl chloride in methylene dichloride was added to the reaction mass. The temperature of reaction mass was then raised to about 25C to about 30C and stirred for about 10-15 hours. After completion of reaction, the reaction mass was quenched in dilute sulfuric acid at about 0C to about 5C. The temperature of the reaction mass was raised to about 20C to about 30C and layers were separated. The aqueous layer was extracted with methylene dichloride. After washing with 5% potassium carbonate solution followed by brine, the organic layer was distilled off completely under reduced pressure to obtain oily residue. To this oily mass, cyclohexane was added at about 50C to about 55C and the reaction mass was cooled gradually to about 20C to about 30C and stirred for 2 hours, the reaction mass was filtered, the residue obtained was dried to get (4S)-3-(pent-4-enoyl)- 4-phenyl-l,3-oxazolidin-2-one (compound Vffl’) as off-white to pale yellow solid. HPLC Purity more than 98.0%., 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; GLENMARK PHARMACEUTICALS LIMITED; NAIR, Ranjeet; BHIRUD, Shekhar Bhaskar; THANKI, Bhavin Prabhudas; BHISE, Sanjay Shashikant; KESHAV, Shrikant Prabhakar; JAGDHANE, Rajendra; CHAUDHARI, Ganesh Bhaskar; GAIKWAD, Nandkumar; GADGE, Sandip; (56 pag.)WO2019/87172; (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

General procedure: Procedure 1: To a solution of alkyne (9.80 mmol, 1.0 equiv) in acetone (10 mL) was added NBS (10.78 mmol, 1.1 equiv) and AgNO3 (0.98 mmol, 0.1 equiv). The resulting solution was stirred under nitrogen at room temperature for 4 h. After removing excess acetone the reaction was quenched with water and extracted with petroleum ether three times, dried over MgSO4, and concentrated under reduced pressure. The residue was eluted through a short silica column (petroleum ether) to obtain the bromoalkyne. To a dried flask was added 2-oxazolidone (4.8 mmol, 1.2 equiv), CuSO4¡¤5H2O (100 mg, 0.4 mmol, 0.1 equiv), 1,10-phenanthroline (144 mg, 0.8 mmol, 0.2 equiv) and K2CO3 (1.38 g, 10.0 mmol, 2.5 equiv), bromoalkyne (4.0 mmol, 1.0 equiv) and this mixture was subsequently treated with anhydrous toluene (10 mL). The flask was charged with nitrogen, and the solution was heated at 80 ¡ãC overnight. After completion, the crude reaction mixture was cooled to room temperature, filtered and concentrated in vacuo. Purification of the crude residue using silica gel flash column chromatography yielded the pure ynamides., 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; Wang, Wan-Shu; Chen, Ping; Tang, Yu; Tetrahedron; vol. 73; 19; (2017); p. 2731 – 2739;,
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

To a solution of Intermediate 1H (1.4 g, 4.8 mmol) in THF (15 mL) was added Et3(1.3 mL, 9.6 mmol). The reaction mixture was cooled to 0 C and trimethylacetyl chloride (0.713 mL, 5.8 mmol) was added dropwise and the resulting solution stirred for 30 min at 0 C. In a separate flask, (R)-4-phenyloxazolidin-2-one (3, 1.01 g, 6.24 mmol) in THF (45 mL) at 0 C was treated with 1 M LiHMDS solution in THF (dropwise addition of 6.24 mL, 6.24 mmol) and stirred at 0C. 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 100% gradient to giveIntermediate II as a white foam in 83% yield, m/z ( +H)+= 433.3.1H- MR (400 MHz; CDCls): delta 8.80 (d, J= 4.5 Hz, 1H), 8.11 (dd, J= 9.1, 5.7 Hz, 1H), 7.63 (dd, J= 10.5, 2.5 Hz, 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

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

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; BALOG, James Aaron; CHERNEY, Emily Charlotte; SHAN, Weifang; WILLIAMS, David K.; ZHANG, Liping; (87 pag.)WO2019/74822; (2019); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

497-25-6, Oxazolidin-2-one is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

2-oxazolidinone (2 g, 23mmol) was dissolved in 15 mL of dry DMF at 0 C with 1.3 eq. of NaH (28 mmol, 1.15 g). The solution was stirred during 1 h, then 1.5 eq. (32 mmol, 3.68 mL) of propargyl bromide diluted in 7 mL of DMF was dropwised during 40 min at 0 C. After additional 20 min, the reaction was quenched with 1 mL of water, and the solvent removed in vacuo. After work-up (CHCl3/H2O; 30/10; V/V) and purification by chromatography (elution gradient: EP/AcOEt; 8/2 to 4/6; V/V), compound 3 (amber oil) was obtained in quantitative yield. Rf = 0.86 (CHCl3/EtOH; 7/3; V/V). FTMS-ESI calcd for C6H7O2NNa, MNa+ 148.0369, found 148.0363; 1H NMR (DMSO-d6): Oxazolidinone: 4.30 (t, 2H, J = 8.1 Hz, CH2-O), 3.56 (t, 2H, J = 8.1 Hz, CH2-N); Propargyl: 4.00 (d, 2H, J = 2.5 Hz, CH2), 3.32 (t, 1H, J = 2.5 Hz, CH). 13C NMR (DMSO-d6): Oxazolidinone: 157.5 (C=O), 75.4 (CH2-O), 61.9 (CH2-N); Propargyl: 79.9 (C-CH2), 78.1 (C-H), 43.5 (CH2)., 497-25-6

The synthetic route of 497-25-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Vergnaud, Julien; Faugeras, Pierre-Antoine; Chaleix, Vincent; Champavier, Yves; Zerrouki, Rachida; Tetrahedron Letters; vol. 52; 46; (2011); p. 6185 – 6189;,
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.

The compound (4) (30 g, 142.72 mmol) Triethylamine (26 g, 256.91 mmol) was dissolved in dichloromethane (150 ml)Cooling to 5 to 10 C, dropwise addition of pivaloyl chloride (17.3g, 142.62mmol), System has exothermic, 30min drop finished,5 to 10 deg C insulation reaction 2h, To the reaction system was added (S) -4-phenyl-2-oxazolidinone (23.3 g, 142.76 mmol) DMAP (2.4 g, 19.63 mmol), DMF (15 ml),Exothermic The temperature rose to 15 C, Heated to 45 reflux reaction 3h, Down to room temperature, Plus dichloromethane (150 ml), The organic phase was washed with water (60 ml) 1N hydrochloric acid (120 ml) Water (60ml) 2.5% aqueous sodium hydroxide solution (180 ml) Add water (50ml) wash, Organic phase concentrated dry, Plus isopropyl alcohol (60 ml), Stirring for 24 h, Filter, Add isopropyl alcohol (10ml) leaching, To give a white solid, I.e. compound (5) (34.4 g, 68% yield)., 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; Anrun Pharmaceutical (Suzhou) Co., Ltd.; Hong Jian; Wang Jingbing; Xu Xin; Liu Guobin; (15 pag.)CN104513187; (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

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