Heterocyclic Building Blocks-Oxazolidine

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.169048-83-3,(S)-5-(Chloromethyl)oxazolidin-2-one,as a common compound, the synthetic route is as follows.

General procedure: To the solution of 4-amino-6-{7-chloro-3-oxatricyclo[7.3.1.05,13]trideca-1(13),5,7,9,11-pentaen-8-yl}-1,3,5-triazine-2-thiol (17, 399 mg, 1.21 mmol) and N-(2-chloroethyl)methanesulfonamide (381 mg, 2.41 mmol) in N,N-dimethylformamide (20 mL) was added N-ethyldiisopropylamine (631 muL, 3.14 mmol) at room temperature. The resulting mixture was stirred for 2.5 h at 70 C. After cooling to room temperature, the mixture was extracted between ethylacetate and water. The organic layer was washed with water and brine successively, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated by evaporation and the resulting residue was purified by preparative HPLC to give the title compound 62%, a light brown solid). H NMR (400 MHz, DMSO-d6) delta: 3.26 (1H, dd, J = 6.6, 8.8 Hz), 3.38 (1H, dd, J = 14.0, 6.0 Hz), 3.47 (1H, dd, J = 14.0, 6.0 Hz), 3.57 (1H, dd, J = 8.8, 8.8 Hz), 4.79-4. 87 (1H, m), 5.05 (2H, s), 5.06 (2H, s), 7.35 (1H, d, J = 7.1 Hz), 7.43 (1H, d, J = 8.8 Hz), 7.45 (1H, s), 7.53 (1H, dd, J = 8.8, 7.1 Hz), 7.57 (1H, s), 7.91 (2H, s). MS (ESI+) m/z: 430, 432 [M+H]+. HRMS (ESI+) m/z: [M+H]+ calcd for C19H1735ClN5O3S, 430.07351; found, 430.07277, [M+H]+ calcd for C19H1737ClN5O3S, 432.07056; found, 432.06954., 169048-83-3

169048-83-3 (S)-5-(Chloromethyl)oxazolidin-2-one 7058042, aoxazolidine compound, is more and more widely used in various fields.

Reference£º
Article; Suda, Atsushi; Kawasaki, Ken-Ichi; Komiyama, Susumu; Isshiki, Yoshiaki; Yoon, Dong-Oh; Kim, Sung-Jin; Na, Young-Jun; Hasegawa, Kiyoshi; Fukami, Takaaki A.; Sato, Shigeo; Miura, Takaaki; Ono, Naomi; Yamazaki, Toshikazu; Saitoh, Ryoichi; Shimma, Nobuo; Shiratori, Yasuhiko; Tsukuda, Takuo; Bioorganic and Medicinal Chemistry; vol. 22; 2; (2014); p. 892 – 905;,
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 4. (5)-3-((5)-3-(4-Chlorophenyl)-3-(6-methoxypyridin-3-yl)propanoyl)-4-phenyloxazolidin- 2-one To a precooled (0 C) solution of (5)-3-(4-chlorophenyl)-3-(6-methoxypyidin-3- yl)propanoic acid (3.30 g, 11.3 mmol) in THF (30.0 mL) was added pivolyl chloride (1.39 mL, 1 1.3 mmol), DMAP (cat) and triethylamine (3.15 mL, 22.6 mmol) drop-wise and stirred for 1 h. In another precooled (-78 C) suspension of (5)-4-phenyloxazolidin-2-one (2.03 g, 12.4 mmol) in THF (10.0 mL) was added w-BuLi (2.50 M solution in hexanes, 9.30 mL, 14.9 mmol) drop- wise and stirred at -20 C for 1 h. The solution of the above mixed anhydride was added slowly and stirred for additional 3 h. The reaction mixture was quenched with saturated solution of NH4C1 (250 mL) and extracted with EtOAc (2 x 200 mL). The combined EtOAc extracts were washed with brine (200 mL), dried ( a2S04), filtered and concentrated under reduced pressure. The residue was purified on 40 g S1O2 column using using a gradient elution of 0-40% EtOAc in hexanes. Fractions containing the product were combined and concentrated under reduced pressure to provide the product (3.20 g, 65%) as white solid. MS: m/z = 437 (M+H+)., 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.; 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.

99B. (S,E)-3-(Pent-2-enoyl)-4-phenyloxazolidin-2-one To a light suspension of (S)-4-phenyloxazolidin-2-one (3.8 g, 23 mmol), lithium chloride (1.017 g, 24 mmol) and triethylamine (4.32 mL, 31 mmol) in THF (50 mL) at -20 C. was added (E)-pent-2-enoic anhydride (5.09 g, 27.9 mmol) dropwise. After completion of addition, the cold bath was removed and the mixture was allowed to warm to rt. The mixture was stirred at rt for 2.5 days and the resulting thick suspension was diluted with EtOAc. The mixture was washed sequentially with 0.2M HCl, sat’d NaHCO3, water and sat’d NaCl. The organic layer was dried (Na2SO4) and concentrated to give an orange liquid which was purified via silica gel chromatography to afford (the desired product (4.37 g, 76% yield) as a white solid: LC-MS [M+H] 246., 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; Bristol-Myers Squibb Company; Ellsworth, Bruce A.; Shi, Jun; Ewing, William R.; Jurica, Elizabeth A.; Hernandez, Andres S.; Wu, Ximao; US9133163; (2015); B2;,
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.

Preparation of (i?)-3-cinnamoyl-4-phenyloxazolidin-2-one: A THF (50 mL) solution of (i?)-4-phenyloxazolidin-2-one (5.90 g, 36.2 mmol) was cooled to -78 ¡ãC and treated with lithium bis(trimethylsilyl)amide (36.9 mL, 36.9 mmol, 1.0 M in THF) dropwise over 15 minutes. After 15-minute stirring at -78 ¡ãC, a THF (10 mL) solution of cinnamoyl chloride (6.33 g, 38.0 mmol) was then introduced. The mixture was stirred for 1 hour at -78 ¡ãC and 2 hours at ambient temperature before it was quenched with saturated NaHCC>3 (50 mL) and stirred for 1 hour. The mixture was diluted with EtOAc (200 mL), washed with water and brine, dried over MgS04, filtered and concentrated to give the product as a pale yellow solid (10.6 g, 99.9percent yield). MS (apci) m/z = 293.9 (M+H)., 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; 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

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.

[00203] To a solution of Preparation 4H (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 (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 give Preparation 41 as a white foam in 83% yield, m/z (M+H)+ = 433.3. ^-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, 90319-52-1 (R)-4-Phenyloxazolidin-2-one 730425, aoxazolidine compound, is more and more widely used in various fields.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; CHERNEY, Emily Charlotte; ZHANG, Liping; WILLIAMS, David K.; BALOG, James Aaron; (68 pag.)WO2017/192840; (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.

4.1.23 (4S,2E)-3-(4′-Methylpent-2′-enoyl)-4-phenyloxazolidin-2-one 4243,44 Butyllithium (1.60 M in hexanes, 8.24 mL, 20.6 mmol) was added slowly via syringe to a stirring solution of (4S)-4-phenyl-2-oxazolidinone 41 (3.37 g, 20.6 mmol) in THF (30 mL) under an atmosphere of nitrogen at -78 C. The resulting solution was stirred for 20 min at -78 C. A solution of (E)-4-methylpent-2-enoylchloride 40 (3.01 g, 22.8 mmol) in THF (17 mL) was added slowly by syringe. The temperature was maintained at -78 C for 30 min at which stage it was raised to 0 C and the reaction mixture stirred at this temperature for 1.5 h. The reaction mixture was then quenched by the addition of saturated aqueous ammonium chloride (30 mL) and the volatiles were removed under reduced pressure. Ethyl acetate (65 mL) was added, the organic phase separated and washed with saturated aqueous sodium bicarbonate (2*30 mL), brine (30 mL), dried and the solvent removed under reduced pressure to give the crude oxazolidinone 42. Purification by flash chromatography on silica gel eluting with ethyl acetate/hexane (20:80) gave the pure oxazolidinone 42 (4.71 g, 88%) as a white solid: mp 100-102 C (lit., 43 103-104 C); [alpha]D20 +105.8 (c 1.0, CHCl3) {lit., 43 [alpha]D20 +103.1 (c 1.0, CHCl3)}; numax/cm-1 (KBr) 2966, 1778, 1685, 1639; deltaH (300 MHz, CDCl3) 1.06, 1.07 [6H, 2* d, 2* J 6.9, CH(CH3)2], 2.42-2.63 [1H, sym m, CH(CH3)2], 4.27 [1H, dd, A of ABX, J 8.7, 3.9, one of C(5)H2], 4.69 [1H, dd appears as t, B of ABX, J 8.7, one of C(5)H2], 5.49 [1H, dd, X of ABX, J 8.7, 3.9, C(4)H], 7.05 [1H, dd, J 15.3, 6.6, C(3′)H], 7.16-7.46 {6H, m, containing 7.22 [1H, dd, J 15.3, 1.2, C(2′)H], ArH}; deltaC (75.5 MHz, CDCl3) 21.1, 21.2 [2* CH3, CH(CH3)2], 31.4 [CH, CH(CH3)2], 57.7 [CH, C(4)H], 69.9 [CH2, C(5)H2], 117.6 [CH, C(2′)H], 125.9, 128.6, 129.1 (3* CH, aromatic CH), 139.1 (C, quaternary aromatic C), 153.7 (C, C=O), 158.1 [CH, C(3′)H], 164.9 (C, C=O)., 99395-88-7

The synthetic route of 99395-88-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Foley, David A.; O’Leary, Patrick; Buckley, N. Rachael; Lawrence, Simon E.; Maguire, Anita R.; Tetrahedron; vol. 69; 6; (2013); p. 1778 – 1794;,
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

Intermediate 15: [(R)-4-BENZVL-3- (2-HYDROXYMETHYL-3-METHVL-BUTANOYL)-OXAZOLIDINONE] [4-BENZYL-3- (3-METHYLBUTANOYL)-OXAZOLIDINONE] (14) * (26. 1g, 0.1mol) was stirred in dry [DICHLOROMETHANE (400ML)] at [0C] under nitrogen as titanium tetrachloride (1. 0M solution in dichloromethane, 105ml, 0. [105MOL)] was added and the mixture, which contained a yellow precipitate, was stirred a further 15 minutes then [DIISOPROPYLETHYLAMINE (19ML, 0. 11MOL)] was added dropwise, maintaining the temperature below [5C.] The resulting purple solution was stirred for 75 minutes then 1,3, 5-trioxane (9.9g, [0.] 11mol) in [DICHLOROMETHANE] (60ml) was added, and after a further 10 minutes, titanium tetrachloride (1. [OM] in DCM, 105ml, 0. [105MOL)] was added. The mixture was stirred for 2.5 hours at [0C] then quenched by the addition of saturated ammonium chloride (500ml). Water (100ml) and [DICHLOROMETHANE] [(100ML)] were added, the aqueous phase extracted with a further 2 x [100ML DICHLOROMETHANE,] the combined organics dried over [NA2SO4] and evaporated. Recrystallisation from 30% [DICHLOROMETHANE/PETROLEUM] gave 18.7g (64%) of the title compound as a white solid. LCMS RT=2.94minutes [MH+ 292], 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; GLAXO GROUP LIMITED; WO2003/104200; (2003); 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 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 -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 (45)-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%). 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, 1 H), 1.84 (quintet, J- 7.1 Hz, 2H). LC-MS: m/z (ES) 258.2 (MH)+., 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.; NAGABUKURO, Hiroshi; EDMONDSON, Scott, D.; SINHAROY, Mary, Struthers; DENNEY, William, S.; FRENKL, Tara, L.; WO2011/43942; (2011); 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

At the same time, in a seperate flask charged with a solution of (S)-(+)-4-phenyl-2-oxazolidinone (8.86 g, 54 mmol) in anhydrous tetrahydrofuran (130 mL) under nitrogen at -78 C. was added dropwise a solution of n-butyl lithium (22 mL, 54 mmol, 2.5 M in hexanes). The mixture was stirred at -78 C. for 20 minutes and then transferred via a cannula into the reaction flask containing the mixed anhydride at -78 C. The reaction mixture was stirred at 0 C. for 1 hour, then warmed to room temperature and stirred for 18 hours. The mixture was quenched with saturated aqueous ammonium chloride solution (200 mL), concentrated to about half of its original volume under reduced pressure to remove tetrahydrofuran. The remaining mixture was extracted with ethyl acetate (2*250 mL). The organic layer was separated, combined, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by chromatography over silica gel eluted with 2:1 ethyl acetate/hexanes to give (S)-3-((E)-pent-2-enoyl)-4-phenyl-oxazolidin-2-one as a white foam (9.9 g, 75%)., 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; Chu, Xin-Jie; Fotouhi, Nader; Huby, Nicholas J.S.; Kong, Norman; McDermott, Lee Apostle; Moliterni, John; Zhang, Zhuming; US2006/41146; (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.90319-52-1,(R)-4-Phenyloxazolidin-2-one,as a common compound, the synthetic route is as follows.

n-butyllithium (2.5 Min hexane, 13.5 mL, 33.74 mmol, 1.1 eq) was added to a solutionof (R)-4-phenyloxazolidin-2-one (5 g, 30.67 mmol, 1 eq) in dry THF (75 mL) at -50 ‘C under N2atomosphere. After 30 minutes, 2-fuoropropanoyl chloride (3.75 g, 33.74 mmol) was added, and thesolution was stirred for 1 hat -50 ‘C to -60 ‘C. The reaction was then quenched with a saturatedsolution ofNH4Cl, extracted with EtOAc, washed with NaHC03(sat), brine and dried over MgS04?Solvents were removed under reduced pressure. The product was purified over silica (hexane/EtOAc) and recovered as a brown oil (4 g, 55percent). 1H-NMR(CDCl3, 400 MHz): 8 7.35-7.21 (m, 5H), 5.99-5.84 (md, 1 H), 5.42-5.33 (dd, 1 H), 4.72 (dd, 1 H), 4.31(m, 1 H), 1.50 (m, 3 H)., 90319-52-1

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

Reference£º
Patent; PHARMARESOURCES (SHANGHAI) CO., LTD.; CHEN, Ping; PENG, Shaoping; LI, Yinqiang; LI, Dafeng; DONG, Xuejun; (48 pag.)WO2018/32356; (2018); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem