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

In a reaction flask, tetrahydrofuran (50 mL) was added, (S)-4-phenyloxazol-2-one (5.0 g, 30.6 mmol) was added, and the temperature was cooled to -70 C.; under nitrogen gas protection, the internal temperature was maintained at -65-75 C., 2.5 M n-butyllithium (12.9 mL, 32.2 mmol, 1.05 eq) solution was added dropwise, after the addition, the reaction was conducted for half an hour at a maintained temperature; then the internal temperature was maintained at -65-75 C., valeryl chloride (4.1 g, 34.0 mmol, 1.11 eq) was added dropwise and reacted for 1 hour, and TLC was used to detect the disappearance of (S)-4-phenyloxazol-2-one, and treatment was performed; then the temperature was raised to 0 C., 20 mL saturated aqueous ammonium chloride solution was added and quenched by butyl lithium to separate the phase. The organic phase was concentrated under a reduced pressure. The concentrate was dissolved in 50 mL methylene dichloride, washed with water twice (25 mL¡Á2). The organic phase was dried over 10.0 g anhydrous sodium sulfate for 2 hours; filtered and concentrated under a reduced pressure to give the target product as a white solid (7.4 g, yield 97.6%). (0085) 1H NMR (600 MHz, CDCl3) delta 7.38 (dd, J=8.2, 6.6 Hz, 2H), 7.35-7.31 (m, 1H), 7.31-7.27 (m, 2H), 5.42 (dd, J=8.7, 3.7 Hz, 1H), 4.68 (t, J=8.8 Hz, 1H), 4.27 (dd, J=8.9, 3.7 Hz, 1H), 2.93 (td, J=7.4, 2.6 Hz, 2H), 1.63-1.53 (m, 3H), 1.33 (dtd, J=15.1, 7.6, 5.5 Hz, 2H), 0.89 (t, J=7.4 Hz, 3H). MS (ESI): m/z 248.1 [M+H]+. [alpha]D19 +60.0 (c=1.0 g/100 mL, CHCl3)., 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; BEIJING ABLEPHARMTECH CO., LTD.; MA, Liang; (14 pag.)US2019/359583; (2019); 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.

In a separate flask, n-butyllithium (4.6 mL, 11.6 mmol, 2.5 M F in hexanes) was added to (S)-(+)-4-phenyl-2-oxazolidinone (2.0 g, 12.2 mmol) in anhydrous tetrahydrofuran at -78 C. and allowed to stir for 10 minutes. The lithiated oxazolidinone was transfered via cannula to the mixed anhydride at -78 C. and stirring continued for 2 hours. The reaction was quenched with water (25 mL) and extracted with ethyl acetate. The combined extracts were washed with water, brine and dried over sodium sulfate. The crude product was purified by chromatography over silica gel eluted with 2:3 ethyl acetate/hexanes and the resulting solid was recrystallized from ethyl acetate/hexanes to afford (S)-4-phenyl-3-((S)-3-phenyl-butyryl)-oxazolidin-2-one (1.63 g, 88% 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; 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

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 solution of (E)-4- (benzyloxy)but-2-enoic acid 236 (2.5g, 13.01mmol) and triethylamine (1.45g, 14.31 mmol) in anhydrous THF (40 mL) under nitrogen at -78 C was added trimethylacetyl chloride (1.72g, 14.3 lmmol). The reaction mixture was stirred at -78 C for 10 minutes, 0 C for 1 hour, then re-cooled to -78C.At the same time, in a seperate flask charged with a solution of (S)-4-phenyloxazolidin-2- one 237 (0.42g, 2.6mmol) in anhydrous THF (40 mL) under nitrogen at -78 C was added dropwise a solution of LiHMDS (14.31 mL, 14.3 lmmol). 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 crude mixture was quenched with sat. NH4CI (200 mL), and concentrated in vacuo, to about half of its original volume under reduced pressure to remove THF. The remaining mixture was extracted with ethyl acetate (150 mL x 2). The organic layer was separated, combined, dried over anhydrous Na2SC>4 and concentrated to dryness. The residue was purified by silica gel column (PE : EA = 2 : 1) to give 238, (S,E)-3-(4-(benzyloxy)but-2-enoyl)-4-phenyloxazolidin-2-one (3 g, 68% yield). LC-MS (LC method 1): m/z 338 (M+l)+., 99395-88-7

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

Reference£º
Patent; SPERO OPCO; LISTER, Troy; SHARMA, Rajiv; ZABAWA, Thomas; ZAHLER, Robert; (146 pag.)WO2017/189866; (2017); 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

(S) -4-phenyl-2-oxazolidinone was added to a 250 mL three-necked flask, 83 g (48 mmol), DIPEA (15 mL)Anhydrous dichloromethane 144 mL,DMF 3 drops and DMAP catalytic amount, heated to reflux, and slowly dropwise 11.5 g (72 mmol) of methyl chlorocaproate.Reflux reaction for 3 hours,TLC showed that the reaction was complete with 1M dilute hydrochloric acid to terminate the reaction, saturated sodium bicarbonate, saturated brine washing, anhydrous sodium sulfate drying, concentration, sand, the final column chromatography was pure 9.3g, income: 66.15%, mp : 54 C to 56 C

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; Nanjing University of Technology; Wang, YuBin; Xue, xiaojian; Lu, peng; Fan, chen; Qin, Hui; (20 pag.)CN103864658; (2016); B;,
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-oxazolidin-2-one[(4-Methoxybenzyl)thio] acetic acid (1.3 g, 6.1 mmol) was dissolved in dry CH2Cl2 (40 ml) and given O0C. N,N’-Dicyclohexylcarbodiimide (DCC, 6.1 g, 6.1 mmol) and 4- (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 reduced pressure and purified by flash-chromatography (Hex : EtOAc 8:2 then 1:1). This afforded 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, /= 8.6 Hz, 2H), 7.14 (d, /= 8.6 Hz, 2H), 7.32-7.40 (m, 5H).

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

Reference£º
Patent; ASTRAZENECA AB; WO2006/137797; (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.

Synthesis of (R,E)-3-but-2-enoyl-4-phenyloxazolidin-2-one: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, CDCI3/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

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

Reference£º
Patent; ENVIVO PHARMACEUTICALS, INC.; RIPKA, Amy; SHAPIRO, Gideon; MCRINER, Andrew; WO2012/40230; (2012); 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.95530-58-8,(R)-4-Isopropyloxazolidin-2-one,as a common compound, the synthetic route is as follows.

95530-58-8, To a cooled (-10 0C) solution of 8-(4-fluoro-3-methylphenyl)octanoic acid (0.486 g, 1.926 mmol) in 15 mL of THF, were added stepwise triethylamine (0.69 mL, 4.952 mmol) and pivaloyl chloride (0.23 mL, 1.889 mmol). The reaction mixture was stirred at -10 0C for 1 h and then LiCl (0.080 g, 1.889 mmol) and (R)-4-iso- propyloxazolidin-2-one (0.237 g, 1.834 mmol) were added stepwise. After being warmed slowly to room temperature and stirred for overnight, the reaction mixture was diluted with ethyl acetate (80 mL) and washed with saturated NaHCO3 solution and brine. The organic layer was dried (Na2SO4), filtered, and concentrated under reduced pressure. The product was isolated by Flash column chromatography(silica gel column) eluting with 0-100 % dichloromethane/hexanes to give the title compound as colorless oil (0.547 g, 82% yield). GC-MS: tR = 6.9 min; m/z 363 (M+).

95530-58-8 (R)-4-Isopropyloxazolidin-2-one 641505, aoxazolidine compound, is more and more widely used in various fields.

Reference£º
Patent; PANTHERA BIOPHARNA, LLC; WO2008/94592; (2008); 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.

4S)-3-{[(4-Methoxybenzyl)thio]acetyl}-4-phenyI-l,3-oxazolidin-2-one; [(4-Methoxybenzyl)thio] acetic acid (1.3 g, 6.1 mmol) was dissolved in dry CH2Cl2 (40 ml) and given O0C. N,N’-Dicyclohexylcarbodiimide (DCC, 6.1 g, 6.1 mmol) and 4- (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 reduced pressure and purified by flash-chromatography (Hex : EtOAc 8:2 then 1:1). This afforded the title compound.1H-NMR (CDCl3, 200 MHz): delta 3.46-3.59 (m, 3H), 3.74-3.76 (m, 4Hj, 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, / = 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; WO2006/137793; (2006); 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

In three 500ml flask, was added ( s) -4- phenyl-2-oxazolone 20g (0.122mol, 1eq.) And dichloromethane 200ml, cooled to between 0 ~ 10 , was added chlorotrimethylsilane 15.86g (0.146mol, 1.2eq.), kept under stirring at 0 ~ 10 30 minutes, a solution of diisopropylethylamine 39.30g (0.305mol, 2.50eq.), was added dropwise in the temperature control of the material during 0 ~ between 10 , after completion of the dropwiseaddition, stirring was continued for 2 hours at 0 ~ 10 until (s) -4- phenyl-2-oxazolone starting material by TLC the reaction was complete (monitored by TLC conditions: petroleum ether / ethyl acetate acetate = 2/1).acryloyl chloride WAS the then added 15.46 g (0.171 mol, 1.4 eq.), at The temperature at The Control of Material’s at The Addition During the BETWEEN 0 ~ 10 deg.] C, the After Addition at The Complete WAS, WAS added of 1.6 g of anhydrous Tetrabutylammonium fluoride (of TBAF, 6.1 mmol, 0.05 eq.), at The Reaction WAS AT Stirred Room temperature for 2 hours.the After Completion of at The Reaction, Reaction Solution at The WAS Poured INTO ICE 200ml of Water, and Stirred AT Room temperature for 30 minutes, at The Organic Phase WAS Separated, at The Organic Phase WAS Washed the with 10% (wt) WAS Washed the with Sodium bicarbonate Solution, at The Organic Phase WAS Separated, Evaporated to Dryness to give at The crude Product the After at The Organic Phase.Isopropyl alcohol WAS added to at The crude Product 100ml, Stirred AT 25 Suction Filtration hours to 2 deg.] C to give A White Solid Powder, and dried to give Compound at The Product 24.6 g, a yield 93%.1, 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; Jiangsu Hengsheng Pharmaceutical Co., Ltd; Wang, Xilin; Ding, Zunliang; Wu, Huafeng; Wang, Zhe; Chen, Zhikuan; (9 pag.)CN105541742; (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

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 -25 C. 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-1,3-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¡Á300 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, CDCl3): 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, 1H), 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; Berger, Richard; Chang, Lehua; Edmondson, Scott D.; Goble, Stephen D.; Ha, Sookhee Nicole; Kar, Nam Fung; Kopka, Ihor E.; Li, Bing; Morriello, Gregori J.; Moyes, Chris R.; Shen, Dong-Ming; Wang, Liping; Zhu, Cheng; US2009/253705; (2009); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem