Heterocyclic Building Blocks-Oxazolidine

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.

Oxalyl chloride (4.7 mL, 56.1 mmol) was added drop-wise to a mixture of commercially available (?)-3-(4-methoxyphenyl)acrylic acid (B12, 5.0 g, 28.1 mmol) in anhydrous dichloromethane (80 mL) at 0 ¡ãC under nitrogen, after which and anhydrous DMF (0.5 mL) was added. The mixture was slowly warmed to room temperature, stirring for a total of 3 h. (i?)-4-Phenyl-oxazolidin-2-one (4.6 g, 28.1 mmol) and DMAP (100 mg) were added, followed by triethylamine (5.3 mL, 36.5 mmol), and the mixture was heated to 50 ¡ãC to stir for 12 h. The mixture was cooled to room temperature, the solvents were removed under reduced pressure and the residue was triturated with diethyl ether to provide (R,E)-3-[3-(4- methoxyphenyl)acryloyl]-4-phenyloxazolidin-2-one [(i?)B13] as a light yellow solid (8.9 g, 98percent): LCMS (M+H) 324., 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; TREVENA, INC.; CROMBIE SPEERSCHNEIDER, Aimee; YAMASHITA, Dennis SHINJI; PITIS, Philip Michael; HAWKINS, Michael John; LIU, Guodong; MISKOWSKI DAUBERT, Tamara Ann; YUAN, Catherine C.K.; BORBO KARGBO, Robert; HERR, Robert Jason; ROMERO, Donna; (125 pag.)WO2018/152293; (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.90319-52-1,(R)-4-Phenyloxazolidin-2-one,as a common compound, the synthetic route is as follows.

Production Example 1 (4R) -3- (4-Azidobutanoyl)4-phenyloxazolidin-2-one A catalytic amount of dimethylformamide was added to a solution of 4-azidobutyric acid (10.3 g, 80.0 mM) in 100 ml of methylene chloride and, thereafter, thionyl chloride (8.7 ml, 119.5 mM) was added dropwise thereto under ice-cooling. After stirring the reaction mixture at room temperature for one hour, it was evaporated to give a crude acid chloride. A 1.6M solution of n-butyl lithium in hexane (40.2 ml, 64.3 mM) was added dropwise into a solution of (4R)-4-phenyl-2-oxazolidinone (manufactured by Aldrich; 10 g, 61.3 mM) in tetrahydrofuran (80 ml) at -78¡ã C. and the mixture was stirred at the same temperature for 30 minutes. A solution of the previously synthesised acid chloride in tetrahydrofuran (100 ml) was slowly added dropwise into the reaction mixture and the mixture was further stirred for 30 minutes. The reaction was ceased by adding dropwise a saturated aqueous solution of sodium bicarbonate into the reaction mixture followed by warming up to room temperature. The mixture was poured into water followed by extracting with ethyl acetate and the organic layer was washed with a saturated aqueous solution of sodium bicarbonate, water and brine in this order and dried over anhydrous magnesium sulfate. The solvent was removed and the residue was subjected to a silica gel column chromatography (hexane/ethyl acetate=5/1) to give the title compound (17 g, 99percent). 1H-NMR(CD Cl3) delta:1.84(2H,quint,J=7 Hz), 2.88(2H,t,J=7 Hz), 3.25 (2H,t,J=7 Hz),4.24(1H,dd,J=4.9 Hz), 4.65(1H,t,J=7 Hz), 5.36(1H,dd,J=4.9 Hz), 7.22-7.35(5H,m)., 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; Eisai Co., Ltd.; US6218550; (2001); B1;,
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: To a solution of 15a (19.0 g, 107 mmol) in THF (300 mL) cooled to -78 ¡ãC was added n-butyllithium (47.2 mL, 118 mmol, 2.5 M solution in hexane) dropwise. The resulting solution was stirred at this temperature for 20 min before the dropwise addition of propionic anhydride (15.1 mL, 118 mmol). The cooling bath was removed, and the flask was allowed to slowly warm to room temperature and stir for an additional hour whereupon LCMS indicated reaction completion. The reaction was quenched with the addition of sat. NH4Cl. Volatiles were removed in vacuo, and the resulting residue was diluted with DCM. The layers were separated, and the organic layer was washed with water x 2, 1 M NaOH, brine, dried over MgSO4, filtered, and concentrated in vacuo to afford the desired product as a white solid (23.6 g, 94percent yield). Spectral data were in accordance with reported literature values.3, 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
Article; Reed, Carson W.; Fulton, Mark G.; Nance, Kellie D.; Lindsley, Craig W.; Tetrahedron Letters; vol. 60; 10; (2019); p. 743 – 745;,
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 stirred solution of 4 (2 kg, 8 mol) in CH2Cl2 (2 L) was added oxalyl chloride (1.4 L, 16 mol) dropwise at 0 ¡ãC. The resulting solution was stirred at room temperature for another 4 h and concentrated in vacuo. To a stirred solution of (R)-4-phenyloxazolidin-2-one (1.3 kg, 8 mol) and TEA (1.7 L, 12 mol) in CH2Cl2 (4.8 L) at 0 ¡ãC was added the substituted cinnamic chloride in CH2Cl2 (800 mL) dropwise. The mixture was stirred at 0 ¡ãC for 1 h and then raised to room temperature for 3 h when a saturated solution of NH4Cl (600 mL) was added. The aqueous layer was separated, and the organic solution was washed with water (600 mL .x. 3), brine (800 mL), and dried over Na2SO4. The organic solution was evaporated and 2.9 kg of 5 was obtained after recrystallization in EtOH in 93percent yield, mp 143-145 ¡ãC, (c 1.0, CHCl3). 1H NMR (300 MHz, CDCl3): delta 7.86 (d, J = 15.5 Hz, 1H), 7.75 (d, J = 15.3 Hz, 1H), 7.30-7.50 (m, 11H), 7.23 (m, 2H), 7.03 (dd, J = 2.3, 8.6 Hz, 1H), 5.64 (dd, J = 4.0, 9.0 Hz, 1H), 5.15 (s, 2H), 4.85 (t, J = 8.9 Hz, 1H), 4.36 (dd, J = 3.9, 8.8 Hz, 1H). 13C NMR (100 MHz, CDCl3): delta 164.6, 158.9, 153.7, 146.5, 138.9, 136.5, 135.8, 129.8, 129.2, 129.1, 128.6, 128.5, 128.4, 128.1, 127.6, 127.5, 126.0, 125.9, 121.5, 117.4, 117.1, 114.4, 70.0, 69.9, 57.8. HRMS (ESI): Calcd for C25H21NO4Na: 422.1368. Found: 422.1349., 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
Article; Zhang, Qiang; Li, Jian-Feng; Tian, Guang-Hui; Zhang, Rong-Xia; Sun, Jin; Suo, Jin; Feng, Xin; Fang, Du; Jiang, Xiang-Rui; Shen, Jing-Shan; Tetrahedron Asymmetry; vol. 23; 8; (2012); p. 577 – 582;,
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

R-4-phenyl-2-oxazolidone (4 g, 24.5 mmol) was dissolved in 50 mL of dichloromethane, and then triethylamine (5.2 mL, 1.5 eq) was added therein. Subsequently, 2-fluoro-propionyl chloride (1.3 eq) was slowly added dropwise at 0¡ã C.5¡ãAfter the raw materials were completely reacted indicating by TLC, filtering the solid, drying the organic phase by concentration, then 20 mL of methanol was added. The resulting mixture was stirred for 3 h and filtered to give 5 g white solid in a yield of 86.0percent., 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; TOPHARMAN SHANGHAI CO., LTD.; SHANGHAI INSTITUTE OF MATERIA MEDICA, CHINESE ACADEMY OF SCIENCES; TOPHARMAN SHANDONG CO., LTD.; Wang, Guan; Jiang, Xiangrui; Gong, Xudong; Chen, Weiming; Zhu, Fuqiang; Zhang, Rongxia; Zhao, Xianguo; US2015/284351; (2015); 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

A flame-dried 1 L round bottomed flask containing an MTBE solution of 6 (2.8 g, 33 mmol), and 800 mL of THF was chilled by a cold bath at -30 C. (dry ice/30% ethanol in ethylene glycol). The mixture was allowed to stir under nitrogen atmosphere. Distilled triethylamine (12.2 g, 17.0 mL, 120 mmol), and pivaloyl chloride (6.0 g, 6.2 mL, 50 mmol) were added sequentially, and stirring at -30 C. was continued for one hour. LiCl (7.0 g, 170 mmol) was added. After five minutes, (S)-4-phenyloxazolidinone (9.8 g, 60 mmol), and 4-dimethylamino pyridine (408 mg, 3.35 mmol) were added. The whole reaction mixture was allowed to stir overnight at room temperature. The solvents were removed under reduced pressure, and the residue was partitioned between 300 mL of CH2Cl2 and 300 mL water. The aqueous layer was extracted twice with 300 mL portions of CH2Cl2, and the combined organics were dried (Na2SO4), filtered, and concentrated. The residue was chromatographed on silica gel. The initial eluent was 1:1:9 CH2Cl2:ethyl acetate:hexane, followed by elution with 1:3:7 CH2Cl2:ethyl acetate:hexane. The yield of 7 was 7.20 g (31.5 mmol, 95%). Compound 7 is a white solid. mp=118-119 C., [alpha]D+140.0 (c 1.00, THF)., 99395-88-7

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

Reference£º
Patent; University of Delaware; US2009/23916; (2009); 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.

42 g (165 mmol) compound Formula IV, product of Example 1 was solved in 340 ml water- free terahydrofurane, and the vessel was rinsed by dry N2 gas. The solution was cooled to – 200C, and 55 ml (390 mmol) triethyl-amine was added. A mixture of 40 ml tetrahydrofurane and 20.2 ml pivaloyl chloride (19,8 g, 164 mmol) is added trough a drip-funnel for some 30 min at a temperature between -100C and -20 0C. The precipitate-containing mixture was stirred for 2 h at a temperature between -10 and -200C, and then 24,45 g (150 mmol) solid S (+)-4-phenyl-2-oxazolidinone (Va) and 7,5 g (177 mmol) water-free litium-chloride was sprinkled consecutively into it. Then the suspension was stirred for 4 h while it warmed up to 20-25 0C.The reaction was analytically controlled by thin-layer chromatography. When the spot of S (+)-4-phenyl-2-oxazolidinone decreased to 3%, the reaction was stopped with adding 300 ml toluene and 150 ml saturated ammonium-chloride solution. The phases were separated then the aqueous phase was extracted by 50 ml toluene. The united toluenic solution is washed by 2×150 ml 10% citric acid solution, 2×150 ml IM NaOH solution and at last with 3x 150 ml water. The organic phase was dried on anhydrous Na2SO4, the desiccant was filtered out, and the filtrate was evaporated in vacuum. The residue was crystallized at O0C with 150 ml isopropyl-alcohol. The product (Via) was dried in vacuum in the presence of P2O5. Yield: 55.7 g (93%) Melting point: 100-1020C[alpha]jf =+54.3, (c=l, dichloromethane)1H NMR data: (500 MHz, OMSO-d6, 25 0C) delta 1.42-1.56 (m, 2H), 1.76-1.85 (m, 2H), 2.80 (dt, J = 17.2, 7.5 Hz, IH), 2.90 (dt, / = 17.2, 7.5 Hz, IH), 3.61-3.71 (m, 2H), 3.89-3.99 (m, 2H), 4.13 (dd, J = 8.7, 3.6 Hz, IH), 4.71 (t, J = 8.7 Hz, IH), 5.43 (dd, J – 8.7, 3.6 Hz, IH), 7.12-7.19 (m, 2H), 7.23-7.28 (m, 2H), 7.29-7.34 (m, IH), 7.34-7.42 (m, 4H) 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; RICHTER GEDEON VEGYESZETI GYAR RT.; WO2007/72088; (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.497-25-6,Oxazolidin-2-one,as a common compound, the synthetic route is as follows.

497-25-6, General procedure: Alkynylation of gamma-Lactam and Oxazolidin-2-ones with CopperAcetylide; Procedure 2A 5 mL round-bottomed flask was successively charged with the nitrogennucleophile 3 (8.0 mmol), the copper acetylide 2 (2.0 mmol),and MeCN (4 mL). The resulting bright yellow slurry was thentreated with TMEDA (300 muL, 2.0 mmol) and the reaction mixturewas vigorously stirred at r.t. and under an atmosphere of O2 (balloon).After complete disappearance of the alkynylcopper reagent(complete dissolution to a deep blue homogeneous reaction mixture:typically 24-48 h), the crude reaction mixture was concentratedunder vacuum, and the residue was finally purified by flashchromatography over silica gel to afford the desired ynamide 4.

As the paragraph descriping shows that 497-25-6 is playing an increasingly important role.

Reference£º
Article; Theunissen, Cedric; Lecomte, Morgan; Jouvin, Kevin; Laouiti, Anouar; Guissart, Celine; Heimburger, Jeremy; Loire, Estelle; Evano, Gwilherm; Synthesis; vol. 46; 9; (2014); p. 1157 – 1166;,
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

[0791] Synthesis of (R,E)-3-but-2-enoyl-4-phenyloxazolidin-2-one: [0792] To a solution of (R)-4-phenyloxazolidin-2-one (8.30 g, 50.9 mmol) in anhydrous THF (80 mL) were added LiCI (2.48 g, 58.5 mmol) and triethylamine (10.30 g, 101.8 mmol). The resulting solution was stirred at RT for 20 minutes, and was then cooled by an ice-water bath. DMAP (0.63 g, 5.1 mmol) was added followed by drop-wise addition of (E)-but-2-enoyl chloride (6.11 g, 58.5 mmol). The resulting yellow suspension was stirred at 0 ¡ãC for 0.5 h, then at RT for 16 h. Water (160 mL) was added to quench the reaction, and the mixture was extracted with EtOAc (1 x 150 mL, 2 x 100 mL). The combined organic phases were washed with brine (50 mL), dried over magnesium sulfate. The solvent was removed under reduced pressure to give crude product as yellowish oily wax, which was purified by chromatography (0 – 50percent EtO Ac/heptane) to obtain (R,E)-3-but-2-enoyl-4-phenyloxazolidin-2-one as light yellow wax (8.0 g, 68percent). 1H NMR (300 MHz, CDC13/TMS): delta 7.50-7.20 (m, 6H), 7.18-7.00 (m, 1H), 5.48 (dd, 1H, J= 8.7, 3.9 Hz), 4.69 (t, 1H, J= 8.7 Hz), 4.27 (dd, 1H, J= 8.7, 3.9 Hz), 1.93 (dd, 3H, J= 6.7, 1.3 Hz); 13C NMR (75 MHz, CDCI3/TMS): delta 164.2, 153.5, 146.9, 138.9, 128.9, 128.3, 125.7, 121.5, 69.8, 57.6, 18.5.

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; ENVIVO PHARMACEUTICALS, INC.; RIPKA, Amy; SHAPIRO, Gideon; MCRINER, Andrew, J.; BURSAVICH, Matthew, Gregory; WO2013/142269; (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

45)-3-{[(4-Methoxybenzyl)thio]acetyl}-4-phenyl-l,3-oxazoIidin-2-one[(4-Methoxybenzyl)thio]acetic acid (1.3 g, 6.1 mmol) was dissolved in dry CH2Cl2 (40 ml) and given O0C. Nu,Nu’-Dicyclohexylcarbodiimide (DCC, 6.1 g, 6.1 mmol) and 4- 30 (dimethylamino)pyridine (DMAP, 1.6 g, 12.9 mmol) were added and the mixture was stirred for 30 minutes. (S)-(+)-4-Phenyl-2-oxazolidinone (1,0 g, 6.1 mol) was added and the mixture was stirred at room temperature for 24 hours. The mixture was filtrated, concentrated under EPO reduced pressure and purified by flash-chromatography (Hex : EtOAc 8:2 then 1:1). This afforded 1.7 g (77 %) of the title compound.1H-NMR (CDCl3, 200 MHz): delta 3.46-3.59 (m, 3H), 3.74-3.76 (m, 4H), 4.23-4.28 (m, IH), 4.68 (t, J= 8.8 Hz, IH), 5.38-5-42 (m, IH), 6.78 (d, J = 8.6 Hz, 2H), 7.14 (d, J= 8.6 Hz, 2H), 7.32-7.40 (m, 5H)., 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; ASTRAZENECA AB; WO2006/137795; (2006); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem