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 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

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

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

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

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

Step B: Preparation of (R.E)-4-phenyl-3-(3-(3A,5-trifluorophenyl)acryloyl)oxazolidin-2-one: A solution of (R)-4-phenyloxazolidin-2-one (3.92 g, 24.0 mmol) in THF (60 mL) was cooled to -78 C and lithium bis(trimethylsilyl)amide (25.2 mL, 25.2 mmol, 1.0 M in THF) was added dropwise over 10 minutes. The mixture was stirred at -78 C for 45 minutes and a solution of (E)-3-(3,4,5-trifluorophenyl)acryloyl chloride (5.56 g, 25.2 mmol) in THF (15 mL) was added. The mixture was stirred for 17 hours during which time the mixture reached ambient temperature and was poured into cold water (300 mE). The aqueous mixture was extracted with 50% EtOAc/hexanes (3 x) and the combined organic phases were washed with brine, dried over MgSO4lactivated carbon and filtered through a packed Si02 plug capped with a MgSO4 layer (50% EtOAc/hexanes for elution). The filtrate was concentrated in vacuo to afford (R, E)-4-phenyl-3 -(3-(3 ,4,5- trifluorophenyl)acryloyl)oxazolidin-2-one (8.40 g, 100%) as an ivory white solid. ?H NMR (CDC13) 7.84 (d, J 15.7 Hz, 1H), 7.57 (d, J 15.7 Hz, 1H), 7.42-7.33 (m, 5H), 7.21-7.18 (m, 2H), 5.54 (dd, J= 8.7, 3.9 Hz, 1H), 4.75 (t, J 8.8 Hz, 1H), 4.34 (dd, J 8.9, 3.9 Hz, 1H) ppm., 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; BRANDHUBER, Barbara, J.; KERCHER, Timothy; KOLAKOWSKI, Gabrielle, R.; WINSKI, Sharon, L.; WO2014/78323; (2014); 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.

: Preparation of (S)-3-((S)-2-isopropylpent-4-enoyl)-4-benzyloxazolidin-2-one [Show Image] (a) Alkylation with allyl bromide: To a solution of lithium diisopropylamide (23 mL, 46 mmol; 2 M in THF) in anhydrous THF (120 mL), stirred at -78 C under argon, a solution of (S)-4-benzyl-3-(3-methylbutanoyl)oxazolidin-2-one (10.0 g, 38.27 mmol) in anhydrous THF (10 mL) was added and the mixture was stirred for 1.5 h. Then allyl bromide (16.22 g, 134.07 mmol) and DMPU (16 mL) were successively added dropwise. The resulting mixture was continued to stir at -78 C for 2 h and then allowed to reach -45 C at which it was stirred for 4 h. The mixture was allowed to warm to 10 C during 12 h. The reaction was quenched by the addition of saturated aqueous NH4Cl solution (100 mL) and the product was extracted with ethyl acetate (3 ¡Á 250 mL). The combined organic layers were successively washed with ice-cold HCl (1 M, 100 mL), saturated aqueous NaHCO3 solution (2 ¡Á 100 mL), and brine (2 ¡Á 100 mL), and then dried over anhydrous Na2SO4. After removal of the solvents under reduced pressure 14.46 g of crude product were obtained which were further purified by radial chromatography on silica gel (petrolether/ethyl acetate = 10:1) to afford 8.994 g (78 %) of alkylation product as a yellowish oil

145589-03-3, 145589-03-3 (R)-4-Benzyl-3-(3-methylbutanoyl)oxazolidin-2-one 11391340, aoxazolidine compound, is more and more widely used in various fields.

Reference£º
Patent; Krka Tovarna Zdravil, D.D., Novo Mesto; EP2189442; (2010); 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

(b) Alkylation with allyl iodide: To a solution of lithium diisopropylamide (23 mL, 46 mmol; 2 M in THF) in anhydrous THF (120 mL), stirred at -78 C under argon, a solution of (S)-4-benzyl-3-(3-methylbutanoyl)oxazolidin-2-one (10.0 g, 38.27 mmol) in anhydrous THF (10 mL) was added and the mixture was stirred for 1.5 h. To the resulting mixture allyl iodide (10.30 g, 61.32 mmol) was added dropwise and stirring was continued for another 30 min. The resulting mixture was warmed to -45 C at which it was stirred for 15 h. The reaction was quenched by the addition of 1 M aqueous HCl solution (100 mL) and the product was extracted with ethyl acetate (3 ¡Á 250 mL). The combined organic layers were successively washed with ice-cold 1 M aqueous HCl solution (100 mL), saturated aqueous Na-HCO3 solution (2 ¡Á 100 mL), and brine (2 ¡Á 100 mL), and dried over anhydrous Na2SO4. After removal of the solvents under reduced pressure 11.952 g of crude product were obtained which were further purified by radial chromatography on silica gel (petrolether/ethyl acetate = 10:1) to afford 8.302 g (72%) of alkylation product as a colourless oil. 1H NMR (300 MHz, CDCl3) delta: 0.98 (d, 6H), 1.98 (m, 1H), 2.35-2.54 (m, 2H), 2.64 (dd, 1H), 3.31 (dd, 1H), 3.83-3.90 (sym m, 1H), 4.12-4.17 (m), 4.65-4.73 (m, 1H), 5.02 (d, 1H), 5.09 (ddt 1H), 5.76-5.90 (m, 1H), 7.22-7.36 (m, 5H).

145589-03-3, 145589-03-3 (R)-4-Benzyl-3-(3-methylbutanoyl)oxazolidin-2-one 11391340, aoxazolidine compound, is more and more widely used in various fields.

Reference£º
Patent; Krka Tovarna Zdravil, D.D., Novo Mesto; EP2189442; (2010); 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

[00172] To a solution of Preparation H (1.4 g, 4.8 mmol) in THF (15 mL) was added NEt (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, (i?)-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 room temperature and was stirred for 3 hours. 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 give Preparation I as a white foam in 83% yield, m/z (M+H)+ = 433.3. XH-NMR (400 MHz; CDC13): 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, The synthetic route of 90319-52-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; WILLIAMS, David, K.; SHAN, Weifang; ZHANG, Liping; CHERNEY, Emily, Charlotte; BALOG, James, Aaron; (80 pag.)WO2017/192813; (2017); 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.

Step 1): To a solution of (S)-4-phenyl-2-oxazolidinone (41 g, 0.25 mol) in CH2Cl2 (200 ml), was added 4-dimethylaminopyridine (2.5 g, 0.02 mol) and triethylamine (84.7 ml, 0.61 mol) and the reaction mixture was cooled to 0 C. Methyl-4-(chloroformyl)butyrate (50 g, 0.3 mol) was added as a solution in CH2Cl2 (375 ml) dropwise over 1 h, and the reaction was allowed to warm to 22 C. After 17 h, water and H2SO4 (2N, 100 ml), was added the layers were separated, and the organic layer was washed sequentially with NaOH (10%), NaCl (sat’d) and water. The organic layer was dried over MgSO4 and concentrated to obtain a semicrystalline product., 99395-88-7

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

Reference£º
Patent; Schering Corporation; US2005/96307; (2005); 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

(4R)-3-[(2Z)-[4-[(1,1-Dimethylethyl)dimethylsilyl]oxy]-1-oxo-2-buten-1-yl]-4-phenyl-2-oxazolidinone (7) To a solution of acid 6 (6.0 g, 28.2 mmol) in THF (40 mL) at -78 C., was added triethylamine (4.00 mL, 28.2 mmol) followed by trimethylacetyl chloride (3.46 mL, 28.2 mmol) drop-wise. The mixture was warmed to 0 C. over 20 minutes, then the anhydride mixture was cooled to -78 C. Separately, to a solution of (R)-(+)-phenyl-2-oxazolidione (Aldrich) (4.60 g, 28.2 mmol) in THF (40 mL) at -78 C. was carefully added n-BuLi (2.50 M in THF, 11.3 mL, 28.2 mmol) and the mixture was stirred (30 minutes) then transferred to the anhydride solution at -78 C. The final reaction mixture was warmed to room temperature and stirred (over night). The mixture was diluted with EtOAc (200 mL), washed (H2O and brine), dried (Na2SO4), and purified by silica gel column chromatography (hexanes:EtOAc) to yield 7 as a colorless oil (10.2 g, 100% yield). 1H NMR (400 MHz, CDCl3) delta 7.36-7.20 (m, 5H), 7.10 (dt, J=11.6, 2.6 Hz, 1H), 6.50 (dt, J=12.0, 4.6 Hz, 1H), 5.44 (dd, J=8.8, 4.0 Hz, 1H), 4.68-4.59 (m, 3H), 4.22 (dd, J=8.8, 4.0 Hz, 1H), 0.85 (s, 9H), 0.00 (s, 6H). 13C NMR (100 MHz, CDCl3) delta 169.3, 160.6, 158.8, 144.3, 134.5, 134.0, 131.0, 122.0, 75.2, 67.9, 62.8, 31.1, 23.4, 0.00. ESI (+VE) m/z: 384.1 (M+Na)+. HR-ESI cacld for C19H28NO4Si (M+Na)+: 362.1782, Found: 362.1789.

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; The United States of America, as represented by the Secretary, Department of Health & Human Services; Burke, Jr., Terrence R.; Liu, Fa; Lee, Kyung S.; Park, Jung-Eun; (182 pag.)US10266565; (2019); B2;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem