Heterocyclic Building Blocks-Oxazolidine

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 a precooled (0 C) solution of (S)-3-(4-chlorophenyl)-3-(5- (trifluoromethyl)pyridin-3-yl)acrylicacid (1.30 g, 3.94 mmol) in THF (10.0 mL) was added pivolyl chloride (570 mg, 4.73 mmol), DMAP (cat), followed by triethylamine (796 mg, 7.88 mmol) and stirred for 1 h. In another precooled (0 C) suspension of 60% NaH (7.88 mmol) in THF, was added (S)-4-phenyloxazolidin-2-one (772 mg, 4.73 mmol) in THF (10.0 mL) drop- wise and stirred at 0 C for 1 h. The mixed anhydride was added to the reaction mixture and stirred for another 5 h. The reaction mixture was quenched with water (20.0 mL) and extracted with EtOAc (2 x 100 mL). The combined EtOAc extracts were washed with brine (100 mL), dried (Na2S04), filtered, and concentrated under reduced pressure. The residue was purified on 12 g S1O2 using a gradient elution of 0-20% EtOAc in hexanes. Fractions containing the product were combined and concentrated under reduced pressure to provide the product (1.40 g, 76%) as a white solid. MS: m/z = 475 (M+H+)., 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; MERCK SHARP & DOHME CORP.; MSD R&D (CHINA) CO., LTD; WILLIAMS, Peter D.; MCCAULEY, John A.; BENNETT, David Jonathan; BUNGARD, Christopher J.; CHANG, Lehua; CHU, Xin-Jie; DWYER, Michael P.; HOLLOWAY, M. Katharine; KEERTIKAR, Kartik M.; LOUGHRAN, H. Marie; MANIKOWSKI, Jesse J.; MORRIELLO, Gregori J.; SHEN, Dong-Ming; SHERER, Edward C.; SCHULZ, Jurgen; WADDELL, Sherman Tim; WISCOUNT, Catherine M.; ZORN, Nicolas; TUMMANAPALLI, Satyanarayana; SIVALENKA, Vijayasaradhi; HU, Bin; JI, Tao; ZHONG, Bin; WO2015/13835; (2015); 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.

MTBE was added to the 1L reaction flask, 69.78 g pentanoic acid (Compound 1a, 1.2 eq.), Sodium bicarbonate (19.1 g, 2.7 eq), nitrogen was cooled to -40 .Specter pivaloyl chloride was slowly added dropwise 82.38 (compound 3a, 1.2 equiv).Kept stirring at -40 10 hours, 31.38 g of anhydrous lithium chloride (1.3 eq.).(S) -4- phenyl-oxazolidin-2-one (compound 2b, 92.91 g) was formulated into a solution of methyl t-butyl ether, was slowly added dropwise to the reaction solution.Warmed to 35 ~ 40 , stirring was continued for 4 hours.Filtered, the filtrate was added sodium hydroxide solution, and sufficiently stirred, the solvent was evaporated under reduced pressure and extracted with a solvent.The organic layer was washed with dilute hydrochloric acid, saturated brine, dried, filtered, and solvent removal, to obtain 125 g of colorless oil (S) -4- phenyl-3-pentanoyl-oxazolidin-2-one (Compound 4b, 90% purity, 89% 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; Shanghai Huaxingxi Pharmaceutical Technology Co., Ltd; Fan, Penggao; Rao, Weijun; Jiang, Rongying; (11 pag.)CN106008411; (2016); A;,
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 a solution of 69.0 g (615 mmol) of 5-hexynoic acid and 214 mL (1540 mmol) of triethylaraine in 1.0 L of ar ydrous tetrahydrofuran at -25C 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 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, IE), 4.28 (dd, J= 92, 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

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

Reference£º
Patent; MERCK SHARP & DOHME CORP.; BERGER, Richard; EDMONDSON, Scott, D.; HARPER, Bart, H.; WO2011/137054; (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.90319-52-1,(R)-4-Phenyloxazolidin-2-one,as a common compound, the synthetic route is as follows.

Step 4. (R, ?)-4-Phenyl-3-(3-(2,2- -4-yl)acryloyl)oxazolidin-2-one To the solution of (is)-3-(2,2-dimethyltetrahydro-2H-pyran-4-yl)acrylic acid (9 g, 48.9 mmol) in 350 ml of THF was added TEA (7.49 mL, 53.7 mmol) and the resulting solution was stirred under 2 atmosphere and cooled to -10¡ãC (ice/salt water bath). Piv-Cl (6.37 mL, 51.8 mmol) was then added dropwise via syringe over 5 minutes, a thick precipitate formed, this resulting suspension (A) was stirred at -10¡ãC for 15 min then cooled to -78¡ãC. (R)-4-phenyloxazolidin-2- one (9.01 g, 55.2 mmol) was charged to a separate 500 mL round bottom flask and was dissolved in THF (150 mL) and the resulting solution was stirred and cooled to -78¡ãC under 2 atmosphere. n-BuLi (20.52 mL of a 2.5 M solution in hexane) was then added dropwise via syringe over 5 minutes, to which a precipitate formed and this resulting suspension (B) was stirred at -78¡ãC for 10 min. Then solution A (cooled at -78¡ãC) was then added to solution B via cannula over about 5 minutes. The resulting mixture was then stirred at -78¡ãC for 10 minutes and then the cooling bath was removed and the mixture was stirred for 1.5 h while it gradually warmed up to room temperature. The reaction mixture was poured into a 1000 mL Erlenmeyer flask and was diluted with EtOAc (400mL). This solution was then extracted with water (2 x 300 mL) and washed by brine (300 mL), then dried over sodium sulfate, filtered, and stripped in vacuo to give a clear oil. The oil was taken up in DCM and purified via Biotage (RediSep 220 g silica gel) eluting with a gradient of 0-60percent ethyl acetate in hexane. The tubes containing the product were collected and the solvent removed under reduced pressure to afford the product as a white solid (10.12 g, 62.9percent). MS: m/z = 330 (M+H+)., 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; MERCK SHARP & DOHME CORP.; MSD R&D (CHINA) CO. LTD.; WILLIAMS, Peter, D.; MCCAULEY, John, A.; BENNETT, David, J.; BUNGARD, Christopher, J.; CHANG, Lehua; CHU, Xin-Jie; DWYER, Michael, P.; HOLLOWAY, M. Katherine; KEERTIKAR, Kartik, M.; LOUGHRAN, H. Marie; MANIKOWSKI, Jesse, J.; MORRIELLO, Gregori, J.; SHEN, Dong-Ming; SHERER, Edward, C.; SCHULZ, Jurgen; WADDELL, Sherman Tim; WISCOUNT, Catherine, M.; ZORN, Nicolas; SATYANARAYANA, Tummanapalli; VIJAYASARADHI, Sivalenka; HU, Bin; JI, Tao; ZHONG, Bin; WO2015/17393; (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.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

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 a solution of sodium hydride (13.5 g) in tetrahydrofuran (920 mL) was added (4S)-4-phenyl-1,3-oxazolidin-2-one (50 g) portionwise at room temperature, and the resulted mixture was stirred for 1 hour. This reaction solution is referred to as Solution A. In a separate reaction vessel, a solution of chloroacetyl chloride (36.6 mL) in tetrahydrofuran (308 mL) was cooled to 0 C, and the above Solution A was added dropwise in about 5 mL for each portion. After stirred at 0 C for 1 hour, water (300 mL) was slowly added to the reaction solution. The resulted mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, then dried over sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure, the obtained residue was dissolved in dichloromethane (500 mL). To the resulted solution was added p-methoxybenzylthiol (47.2 g) at room temperature, followed by adding triethylamine (64 mL) dropwise using a dropping funnel over 1.5 hours. The resulted solution was then stirred at room temperature overnight. Water (300 mL) and dichloromethane (100 mL) were added to the reaction solution to separate the organic layer and the organic layer was then washed with brine. The organic layer was dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane = 1/5 ? 1/3 ? 1/2) to obtain the title compound (90 g, 82% yield for 2 steps). The NMR data of this compound is shown below. 1H-NMR (400 MHz, CDCl3): delta (ppm) = 3.49-3.61 (m, 3H), 3.77-3.81 (m, 1H), 3.78 (s, 3H), 4.28 (dd, 1H, J = 8.9, 3.9 Hz), 4.62 (dd, 1H, J = 8.9 Hz), 5.43 (dd, 1H, J = 8.9, 3.9 Hz), 6.78-6.81 (m, 2H), 7.14-7.18 (m, 2H), 7.34-7.43 (m, 5H)., 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; Teijin Pharma Limited; EP2133347; (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.90319-52-1,(R)-4-Phenyloxazolidin-2-one,as a common compound, the synthetic route is as follows.

To a solution of 4-(2-(4-fluorophenyl)-5,5-dimethyl-1,3-dioxan-2-yl)butanoicacid (10 g, 0.034 mol) in dichloromethane(50 mL) was added triethyl amine (8.5 ml,0.061 mol) andpivaloyl chloride (5.05 ml,0.041 mol) atroom temperature and stirred for 3h at the sametemperature. To the above reaction mixture R-4-phenyloxazolidinone(6.04 g, 0.037 mol) and LiCl(5.82 g, 0.137 mol) were added and heated to45 ¡ãC. The reaction mixture was maintained for 7h at 45 ¡ãC.After cooling to room temperature water was added, and theorganic layer was separated. The aqueous layer was washed withdichloromethane, and the combined organic extracts were driedover anhydrous Na2SO4 andconcentrated under reduced pressure to give the crudecompound, which was crystallized from hexane and methyltert-butyl ether to give titled compound as a white crystalline solid (11.8 g, 0.027 mol, 78.6percent).?m.p. 73-74oC;[alpha]20 D -57.3 (c 0.3, CH2Cl2); 1H NMR(400 MHz, CDCl3) deltaH (ppm):0.55 (s, 3H), 1.22 (s, 3H), 1.71-1.75(m, 4H), 2.84-2.89 (m, 2H), 3.37 (dd, 4H, J = 14.4,11.2 Hz), 4.20 (dd, 1H, J = 8.8,3.6 Hz), 4.63 (t, 1H, J = 8.8Hz), 5.35 (dd, 1H, J = 8.8,3.2 Hz), 7.01-7.05 (m, 2H), 7.25-7.28 (m, 2H), 7.32-7.38 (m, 5H). ESI-MS:m/z. Calcd.: 441.20; Found: 442.26 [M+H]+.Anal. Calcd. for C25H28FNO5: C, 68.01percent;H, 6.39percent; N, 3.17percent; F, 4.30percent Found C, 68.05percent; H,6.31percent; N, 3.13percent; F, 4.32percent., 90319-52-1

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

Reference£º
Article; Ren, Yun; Li, Renjun; Deng, Yong; Guan, Mei; Wu, Yong; Hai, Li; Tetrahedron Letters; vol. 54; 48; (2013); p. 6443 – 6446;,
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

General procedure: In a round bottom flask dimethyl sulfoxide (50 ml) was added, followed by 1,3 dibromopropane (61.7 g, 306 mmol) and powdered potassium hydroxide (4.47 g, 80 mmol).[13] The reaction mixture was cooled to 15-20 C. To the cooled reaction mixture, was added (S)-4-phenyloxazolidin-2-one (10 g, 61.3 mmol) in 4 to 5 lots at an interval of 5 min each. The reaction mixture was stirred further at 15-20 C for 3-4h. Water (150 ml) was then added to the reaction mixture and it was extracted in dichloromethane (200 ml). The organic layer was concentrated on laboratory rotary evaporator. The resultant residue was purified on silica gel column using cyclohexane/ethyl acetate to get (1a) as colorless oil. Yield: 13.1 g (75%). 1b-1f were prepared in the same manneras 1a., 99395-88-7

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

Reference£º
Article; Nehate, Sagar P.; Godbole, Himanshu M.; Singh, Girij P.; Mathew, Jessy E.; Shenoy, Gautham G.; Synthetic Communications; vol. 48; 18; (2018); p. 2435 – 2440;,
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 the mixture of n-valeric acid (156.5 g) and dichloromethane (1000 ml), (S)-4- phenyloxazoldin-2-one compound of formula-6a (200 g) and 4-dimethylaminopyridine (29.9 g) were added at 25-30C and stirred for 10 minutes at same temperature. The reaction mixture was cooled to 5-10C. A solution of N,N’-dicyclohexylcarbodiimide (316.1 g) in 200 ml of dichloromethane was slowly added to the reaction mixture at 5-10C and stirred for 12 hours at the same temperature. Cooled the reaction mixture to 0-5C and washed the reaction mixture with aqueous HC1 solution followed by water. The obtained organic layer was washed with aqueous sodium carbonate solution followed by water. Distilled off the solvent completely from the organic layer under reduced pressure and co-distilled with n-heptane. To the obtained residue 1600 ml of n-heptane was added at 25-30C. Heated the reaction mixture to 50-55C and stirred for 15 minutes. The reaction mixture was slowly cooled to 0- 5C and stirred for 2 hours at the same temperature. Filtered the precipitated solid, washed with n-heptane and dried to get the title compound.Yield: 243.6 g. M.R.: 42-45C., 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; MSN LABORATORIES PRIVATE LIMITED, R&D CENTER; SRINIVASAN, Thirumalai Rajan; SAJJA, Eswaraiah; REVU, Satyanarayana; CHERKUPALLY, Prabhakar; (59 pag.)WO2018/220646; (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.145589-03-3,(R)-4-Benzyl-3-(3-methylbutanoyl)oxazolidin-2-one,as a common compound, the synthetic route is as follows.

General procedure: A solution of sodium bis(trimethylsilyl)amide in n-hexane (1.03 M, 164 mL, 169 mmol) was added to a solution of 11c (32.9 g, 141 mmol) in THF (330 mL) under N2 atmosphere and at -78 C over 45 min, and the mixture was stirred at the same temperature for 30 min. Then, a solution of benzyl (2E)-4-bromobut-2-en-1-yl ether (35.5 g, 148 mmol) in THF (80 mL) was added to the above solution over 30 min, and the mixture was stirred at the same temperature for 30 min. The reaction mixture was raised to -40 C and further stirred for 4 h. Saturated NH4Cl aqueous solution (100 mL) was added to the reaction mixture, and the mixture was further stirred at room temperature for 1 h. The reaction mixture was concentrated under reduced pressure and diluted with water (500 mL), followed by extraction with AcOEt. Then, the organic layer was washed with water and brine, and dried over anhydrous MgSO4. After filtration, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent, n-hexane/AcOEt = 7:1-2:1) to obtain (4S)-4-benzyl-3-[(2R,4E)-6-(benzyloxy)-2-methylhex-4-enoyl]-1,3-oxazolidin-2-one (37.9 g, 69%, 99% ee) as a colorless liquid., 145589-03-3

The synthetic route of 145589-03-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Nakamura, Yuji; Fujimoto, Teppei; Ogawa, Yasuyuki; Namiki, Hidenori; Suzuki, Sayaka; Asano, Masayoshi; Sugita, Chie; Mochizuki, Akiyoshi; Miyazaki, Shojiro; Tamaki, Kazuhiko; Nagai, Yoko; Inoue, Shin-Ichi; Nagayama, Takahiro; Kato, Mikio; Chiba, Katsuyoshi; Takasuna, Kiyoshi; Nishi, Takahide; Bioorganic and Medicinal Chemistry; vol. 21; 11; (2013); p. 3175 – 3196;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem