Category: 99395-88-7

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.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 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

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

[0728] To a solution of 2-(1-(tert-butoxycarbonyl)-3-vinylazetidin-3-yl)acetic acid (40-3, 1.9 g, 8.12 mmol) in anhydrous THF (30 mL) and cooled to -15 oC was added triethylamine (1.2 mL, 8.93 mmol), followed by dropwise addition of pivaloyl chloride (1.04 mL, 8.52 mmol). The heterogeneous mixture was stirred for 20 min at 0 oC, then re-cooled to -78 oC and stirred for 15 min (solution 1). In a separate flask, (S)-(+)-4-phenyl-2-oxazolidinone (1.32 g, 8.12 mmol) was dissolved in anhydrous THF (30 mL) and cooled to -78 oC. A solution of n-butyl lithium (2.5 M in hexane, 3.2 mL, 8.12 mmol) was added dropwise followed by dropwise addition (15 min) of the mixed anhydride solution (solution 1). The resulting mixture was further stirred for 10 min at -78 oC at which time it was warmed to 0 oC and stirred for 40 min. The reaction mixture was quenched with 10% citric acid (13 mL) and extracted with ethyl acetate (120 mL x 2). The combined organic layers were washed with brine (50 mL x 3), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude residue was purified by CombiFlash column chromatography on silica gel (0- 40% EtOAc in hexane) to afford (S)-4-phenyl-3-(2-(1- (tert-butoxycarbonyl)-3-vinylazetidine-3-yl)acetyl)oxazolidin-2-one (40-4, 2.7 g, 87% yield) as white solid.1H NMR (250 MHz, CDCl3) delta ppm 1.41 (s, 9 H), 3.45 (s, 2 H), 3.77 (t, J = 10.71 Hz, 1 H), 3.82 – 3.93 (m, 2 H), 4.29 (dd, J = 8.90, 3.74 Hz, 1 H), 4.70 (t, J = 8.84 Hz, 1 H), 4.95 – 5.12 (m, 2 H), 5.40 (dd, J = 8.62, 3.57 Hz, 1 H), 6.03 (dd, J = 17.41, 10.71 Hz, 1 H), 7.24 – 7.44 (m, 5 H). MS: [M+H]+ = 386.6.

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

Reference£º
Patent; ACHAOGEN, INC.; COHEN, Frederick; KONRADI, Andrei W.; CHOI, Taylor Ann Joo; MACHAJEWSKI, Timothy D.; KANE, Timothy Robert; HILDEBRANDT, Darin James; (351 pag.)WO2017/223349; (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.

The compounds of formula 21.2g taken with 110ml of DMF was dissolved and replaced with nitrogen, cooled to -10 ~ 0 C under nitrogen, temperature control, input portionwise 16g of lithium hydride, insulation 0.5h, slowly dropwise benzyl chloroformate ester 30.2g, control temperature -10 ~ 0 C, after the addition was complete insulation 1h, warmed to 20 ~ 25 C, into S-4- phenyl-2-oxazolidinone 15.5g, feeding ended, insulation, the reaction was complete, water and methyl tert-butyl ether extracts, standing layer, the organic layer was washed with saturated brine, evaporated under reduced pressure to give an oil. With a mixture of ethyl acetate and hexane to crystallize with stirring, suction filtered and washed with hexane, dried in vacuo to give a white solid product 38.8g, yield 92.9%, HPLC purity 94%. Without further purification, can be used directly in the next step., 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; Zhejiang Jiuzhou Pharmaceutical Co., Ltd; ZHU, GUOLIANG; LI, YUNGUANG; YANG, LIJUN; SUN, LIGUO; CHEN, XIANGYUAN; (8 pag.)CN105461649; (2016); A;,
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

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

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

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

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