Category: 95530-58-8

95530-58-8, The molecularity of an elementary reaction is the number of molecules that collide during that step in the mechanism. If there is only a single reactant molecule in an elementary reaction, that step is designated as unimolecular. 95530-58-8, name is (R)-4-Isopropyloxazolidin-2-one. A new synthetic method of this compound is introduced below.

To a solution of (R) -4-isopropyloxazolidin-2-one (25.0g, 0.194mol, 1.0eq) in anhydrous THF (1150 mL) was added n-BuLi (85.0 mL, 0.213mol, 1.1eq) at -78 under N2and the mixture was stirred at the same temperature for 1 h, a large number of white solids formed. Then propionyl chloride (20.0 mL, 0.232mol, 1.2eq) was added at -78 and the mixture was stirred at the same temperature for 1 h. After the consumption of (S) -4-isopropyloxazolidin-2-one monitored by TLC, the solution was poured into saturated ammonium chloride solution (1.2 L) and the mixture was extracted with EA (700 mL, 350 mL ¡Á 2) . The organic extract was washed with 1.0 N NaOH solution (1.0 L) and brine (1.0 L) , dried over anhydrous sodium sulfate, filtered, concentrated in vacuo and purified by SiO2column chromatography (PE : EA = 10: 1) to give the title compound as a colorless oil (32.6 g, 90.8%) . ESI m/z: calcd for C9H17NO3[M+H]+: 186.1, found 186.1.1H NMR (400 MHz, CDCl3) delta 4.48 -4.37 (m, 1H) , 4.27 (t, J = 8.7 Hz, 1H) , 4.21 (dd, J = 9.1, 3.1 Hz, 1H) , 3.04 -2.82 (m, 2H) , 2.45 -2.30 (m, 1H) , 1.17 (t, J = 7.4 Hz, 3H) , 0.90 (dd, J = 17.1, 7.0 Hz, 6H) .

Any one of these steps may be slow and thus may serve as the rate determining step. In general, however, in the presence of the catalyst, the overall rate of the reaction is faster than it would be if the reactants were in the gas or liquid phase.

Reference£º
Patent; HANGZHOU DAC BIOTECH CO. LTD; ZHAO, Robert Yongxin; YANG, Qingliang; HUANG, Yuanyuan; ZHAO, Linyao; GAI, Shun; YE, Hangbo; LEI, Jun; XU, Yifang; CAO, Mingjun; GUO, Huihui; JIA, Junxiang; TONG, Qianqian; LI, Wenjun; ZHOU, Xiaomai; XIE, Hongsheng; BAI, Lu; CAI, Xiang; ZHUO, Xiaotao; ZHANG, Xiuzheng; ZHENG, Jun; (424 pag.)WO2019/127607; (2019); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

A heterogeneous catalyst is a catalyst that is present in a different phase than the reactants. Such catalysts generally function by furnishing an active surface upon which a reaction can occur. 95530-58-8, name is (R)-4-Isopropyloxazolidin-2-one, introduce a new downstream synthesis route as follows., 95530-58-8

95530-58-8, General procedure: n-BuLi (2.89M, 7.12mL, 20.6mmol) was added dropwise over 15min to a cold (-78C), stirred solution of (R)-4-isopropyloxazolidin-2-one 3 (2.5g, 19.6mmol) in dry THF (80mL), and the mixture was stirred at -78C for 30min. Octanoyl chloride (3.67mL, 21.5mmol) was then added dropwise, and the resulting mixture was stirred at -78C for 20min, then warmed to -10C for 2h. The mixture was quenched with 1M aqueous K2CO3 (100mL) and warmed to room temperature. The crude products were extracted with hexanes (2¡Á100mL), and the combined hexane extracts were washed with water and brine, dried, and concentrated. The residue was purified by flash chromatography on silica gel (50g). Elution with hexane/EtOAc (9:1) afforded 4.93g (19.3mmol, 98%) of (R)- 4 as a colorless oil, numax (neat): 2958 (m), 2927 (s), 2854 (m), 1777 (s), 1699 (s), 1487 (w), 1465 (m), 1384 (s), 1301 (m), 1269 (w), 1232 (m), 1204 (s), 1120 (w), 1091 (w), 1059 (m), 1020 (m), 971 (w), 773 (m), 723 (w), 708 (w); ?H (CDCl3): 0.78 (3H, m), 0.82 (6H, d, J=6.2Hz), 1.18 (6H, m), 1.55 (2H, m), 2.28 (1H, m), 2.74 (1H, pseudoquintet, J=6.2Hz), 2.89 (1H, pseudoquintet, J=6.4Hz), 4.11 (1H, dd, J=16, 4Hz), 4.18 (1H, pseudotriplet, J=8.4Hz), 4.34 (1H, m); ?C (CDCl3): 14.0, 14.9, 18.0, 23.0, 24.9, 28.2, 29.3, 31.9, 35.8, 58.5, 63.5, 154, 173.8; GC-MS [column: DB-5MS, 5% phenylmethylsiloxane, 30m¡Á0.25mm id; carrier gas, He; temp: 50-280C (10C/min)]: tR: 19.43min (100%); MS of 4 (70eV, EI); m/z: 255 (1, M+), 212 (2), 184 (5), 171 (8), 142 (1), 127 (17), 109 (3), 85 (9), 71 (8), 57 (42), 41 (47).

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Reference£º
Article; Bello, Jan E.; Millar, Jocelyn G.; Tetrahedron Asymmetry; vol. 24; 13-14; (2013); p. 822 – 826;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

The molecularity of an elementary reaction is the number of molecules that collide during that step in the mechanism., 95530-58-8, If there is only a single reactant molecule in an elementary reaction, that step is designated as unimolecular. 95530-58-8, name is (R)-4-Isopropyloxazolidin-2-one. A new synthetic method of this compound is introduced below.

A mixture of 2-(3-bromo-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (600 mg, 1.7 mmol), (R)-4-isopropyl-2-oxazolidinone (322 mg, 2.5 mmol), copper(I) iodide (96 mg, 0.5 mmol), N,N-dimethylglycine hydrochloride (140 mg, 1.0 mmol) and potassium carbonate (923 mg, 6.7 mmol) in dimethyl sulfoxide (5 mL) was stirred at 120 C. for 16 h. Then the reaction mixture cooled to room temperature. The reaction mixture was extracted with ethyl acetate (2¡Á150 mL), washed with water (2¡Á50 mL) and saturated aqueous ammonium chloride solution (2¡Á50 mL), dried over anhydrous sodium sulfate and then concentrated in vacuo. Purification by Waters automated flash system (column: Xterra 30 mm¡Á100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% ammonium hydroxide in water) afforded 2-[3-((R)-4-isopropyl-2-oxo-oxazolidin-3-yl)-phenyl]-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (555 mg, 80%) as a white solid: LC/MS m/e calcd for C24H28N2O4 (M+H)+: 409.50, observed: 409.1.

Any one of these steps may be slow and thus may serve as the rate determining step. In general, however, in the presence of the catalyst, the overall rate of the reaction is faster than it would be if the reactants were in the gas or liquid phase.

Reference£º
Patent; Chen, Li; Feng, Lichun; Huang, Mengwei; Liu, Yongfu; Wu, Guolong; Wu, Jim Zhen; Zhou, Mingwei; US2011/257151; (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.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

95530-58-8, (R)-4-Isopropyloxazolidin-2-one is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

95530-58-8, To a solution of hex-5-enoic acid (11.24 g, 87.0 mmol), (4R)-4-isopropyl-1, 3-oxazolidin- 2-one (12.91 g, 113. 1 mmol) and DMAP (1. 06 g, 8.70 mmol) in CH2CI2, was added DCC (23.33 g, 113. 1 mmol) at 0 C and the mixture was stirred at 0 C for 15 min. Then the mixture was stirred at room temperature overnight and was filtered through a pad of celite and the filtrate was washed with sat. NaHCO3aq. The organic layer was dried over Na2SO4, filtered and evaporated. The crude product was purified by silica gel column chromatography (hexane-AcOEt 20: 1-10: 1) to give the titled compound (16.60 g, 73.7 mmol). 1H NMR (CDCI3) 6 : 5.90-5. 70 (m, 1H), 5.10-4. 95 (m, 2H), 4.50-4. 42 (m, 1H), 4.35-4. 15 (m, 2H), 3.10-2. 80 (m, 2H), 2.46-2. 30 (m, 1H), 2.20-2. 08 (m, 2H), 1.90-1. 68 (m, 2H), 0.92 (d, J = 7.1 Hz, 3H), 0.88 (d, J= 6.9 Hz, 3H) ppm

The synthetic route of 95530-58-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; PFIZER JAPAN, INC.; PFIZER INC.; WO2005/80317; (2005); A2;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

95530-58-8, (R)-4-Isopropyloxazolidin-2-one is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,95530-58-8

A mixture of 2-(3-bromo-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (600 mg, 1.7 mmol), (R)-4-isopropyl-2-oxazolidinone (322 mg, 2.5 mmol), copper(I) iodide (96 mg, 0.5 mmol), N,N-dimethylglycine hydrochloride (140 mg, 1.0 mmol) and potassium carbonate (923 mg, 6.7 mmol) in dimethyl sulfoxide (5 mL) was stirred at 120 C. for 16 h. Then the reaction mixture cooled to room temperature. The reaction mixture was extracted with ethyl acetate (2¡Á150 mL), washed with water (2¡Á50 mL) and saturated aqueous ammonium chloride solution (2¡Á50 mL), dried over anhydrous sodium sulfate and then concentrated in vacuo. Purification by Waters automated flash system (column: Xterra 30 mm¡Á100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% ammonium hydroxide in water) afforded 2-[3-((R)-4-isopropyl-2-oxo-oxazolidin-3-yl)-phenyl]-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (555 mg, 80%) as a white solid: LC/MS m/e calcd for C24H28N2O4 (M+H)+: 409.50, observed: 409.1.

The synthetic route of 95530-58-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Chen, Li; Feng, Lichun; Huang, Mengwei; Liu, Yongfu; Wu, Guolong; Wu, Jim Zhen; Zhou, Mingwei; US2011/257151; (2011); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

95530-58-8, (R)-4-Isopropyloxazolidin-2-one is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,95530-58-8

Sodium hydride (55% suspension in oil, 144 mg, 3.31 mmol) was added to a solution of (R) -4-isopropyl-2-oxazolidinone (356 mg, 2.75 mmol) in dry tetrahydrofuran (17 mL) under argon atmosphere. The suspension was stirred for 1 hour at rt, then cooled to [0C] and a solution of 1-bromo-3-chloropropane in dry tetrahydrofuran (3 mL) was added dropwise. After 48 h stirring at [58C] the mixture was quenched with water. The solvent was removed by evaporation under reduced pressure and the residue partitioned between water and dichloromethane. The organic layer was evaporated to dryness. Purification of the residue by silica gel column chromatography, eluting with a mixture of ethyl acetate and n-Heptane (70: 30), afforded [(4R)-3- (3-CHLOROPROPYL)-4-ISOPROPYLOXAZOLIDINON-2-ONE] (401 mg, 71 %). A solution of [(4R)-3- (3-CHLOROPROPYL)-4-ISOPROPYLOXAZOLIDINON-2-ONE] (160 mg, 0.78 mmol) in dry DMF (2 mL) was added to a suspension of potassium carbonate (217 mg, 1.57 mmol) and N-(4-fluorobenzyl)-2-(4-isobutoxyphenyl)- N-piperidin-4-yl-acetamide 103NLS56 (250 mg, 0.63 mmol) in dry DMF (6 mL). After addition of sodium iodide (113 mg, 0.75 mmol) the mixture was stirred overnight at [62C] and partitioned between water and dichloromethane. The organic layer were dried over sodium sulphate, filtered and evaporated to dryness. Purification of the residue by silica gel column chromatography, eluting with 5% methanol in dichloromethane, afforded the desired compound (143 mg, 40%). Rf = 0.28 [(MEOH/CH2CL2] 6: 96). LCMS m/z 568 [[M+H] +. IH] NMR (CDCl3, rotamers 0.4 : 0.6) 8 7.20-6. 78 (m, 8H, Ar-H), 4.61-4. 51 (m, 0.6H, pip-H), 4.48 & 4.42 (2s, 2H, benzyl-H), 4.15 (t, 1H, J= 8.8, oxa-H), 4.01 (m, 1H, oxa-H), 3.78-3. 64 (m, 4.2H, pip- H, benzyl-H, oxa-H, CH2OiBu), 3.48 (m, 2.2H, benzyl-H, CONCHCH2), 2.92-2. 79 (m, 3H, pip-H, [CONCH2),] 2.34-2. 22 (m, 2H, [NCH2CH2CH2),] 2.10-1. 96 (m, 3.2H, pip-H, CHiPr, [CHOIBU),] 1.76-1. 50 (m, 6H, pip-H, [NCH2CH2),] 1.32-1. 26 (m, 0.8H, pip-H), 0.99 (m, 6H, [CH3OIBU)] 0.81-0. 87 (m, 6H, [CH3IPR). HPLC TR=] 9.1 min.

As the paragraph descriping shows that 95530-58-8 is playing an increasingly important role.

Reference£º
Patent; ACADIA PHARMACEUTICALS INC.; WO2004/808; (2003); 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.95530-58-8,(R)-4-Isopropyloxazolidin-2-one,as a common compound, the synthetic route is as follows.,95530-58-8

To a mixture of ethyl 4-iodobenzoate (5.8 mL), (R)-4-isopropyloxazolidin-2-one (5 g), potassium carbonate (15 g) and copper (I) iodide (1.3 g) were added toluene (35 mL) and N,N’-dimethylethylenediamine (1.5 mL), and the mixture was refluxed for 8 hr. After cooling, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated. The residue was dissolved in methanol (35 mL) and 1,4-dioxane (35 mL), 1N aqueous sodium hydroxide solution (70 mL) was added, and the mixture was stirred at room temperature overnight. 1N hydrochloric acid (70 mL) was added, and the mixture was filtered to give the title compound (9 g).

The synthetic route of 95530-58-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Mitsubishi Tanabe Pharma Corporation; EP2364975; (2011); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

95530-58-8, (R)-4-Isopropyloxazolidin-2-one is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,95530-58-8

To a solution of (R) -4-isopropyloxazolidin-2-one (25.0g, 0.194mol, 1.0eq) in anhydrous THF (1150 mL) was added n-BuLi (85.0 mL, 0.213mol, 1.1eq) at -78 under N2and the mixture was stirred at the same temperature for 1 h, a large number of white solids formed. Then propionyl chloride (20.0 mL, 0.232mol, 1.2eq) was added at -78 and the mixture was stirred at the same temperature for 1 h. After the consumption of (S) -4-isopropyloxazolidin-2-one monitored by TLC, the solution was poured into saturated ammonium chloride solution (1.2 L) and the mixture was extracted with EA (700 mL, 350 mL ¡Á 2) . The organic extract was washed with 1.0 N NaOH solution (1.0 L) and brine (1.0 L) , dried over anhydrous sodium sulfate, filtered, concentrated in vacuo and purified by SiO2column chromatography (PE : EA = 10: 1) to give the title compound as a colorless oil (32.6 g, 90.8%) . ESI m/z: calcd for C9H17NO3[M+H]+: 186.1, found 186.1.1H NMR (400 MHz, CDCl3) delta 4.48 -4.37 (m, 1H) , 4.27 (t, J = 8.7 Hz, 1H) , 4.21 (dd, J = 9.1, 3.1 Hz, 1H) , 3.04 -2.82 (m, 2H) , 2.45 -2.30 (m, 1H) , 1.17 (t, J = 7.4 Hz, 3H) , 0.90 (dd, J = 17.1, 7.0 Hz, 6H) .

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

Reference£º
Patent; HANGZHOU DAC BIOTECH CO. LTD; ZHAO, Robert Yongxin; YANG, Qingliang; HUANG, Yuanyuan; ZHAO, Linyao; GAI, Shun; YE, Hangbo; LEI, Jun; XU, Yifang; CAO, Mingjun; GUO, Huihui; JIA, Junxiang; TONG, Qianqian; LI, Wenjun; ZHOU, Xiaomai; XIE, Hongsheng; BAI, Lu; CAI, Xiang; ZHUO, Xiaotao; ZHANG, Xiuzheng; ZHENG, Jun; (424 pag.)WO2019/127607; (2019); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

95530-58-8,95530-58-8, (R)-4-Isopropyloxazolidin-2-one is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of (R)-4-isopropyl-oxazolidin-2-one (1.3g, 10 mmol) and NaH (480 mg, 60% oildispersion, 12 mmol) in THF (50 ml) was stirred at rt for 2h. then cooled to 0C. A solution ofbromoacetonitrile (1.4 ml, 20 mmol) in THF (30 ml) was added slowly to the reaction mixture. Theresulting mixture was stirred at rt for overnight. The mixture was treated with small amount of waterand then the mixture was passed through a silica pad. The filtrate was concentrated and the residue20 was subjected to a short column to give the crude product. The process was repeated and bothcrude product were combined and further purified by another short column to give the product(3.3g).To a solution of above product (3.3g, 19 mmol) in THF (40 ml) at ooc was added a solution ofBH3THF in THF (1M, 200 ml). The resulting mixture was stirred at ooc for 30 min. then at rt for 4h.25 The mixture was then cooled to ooc again and treated with cold HCI (6 N, 20 ml) to strong acidic pH.The organic solvent was removed under reduced pressure. The residue was treated with NaOH (4 N,-40 ml) to pH>10, then extracted with EtOAc (5 x 80 ml) and DCM (5 x 80 ml). The combined extracts from both solvent were dried (Na2S04) and concentrated. EtOAc concentrate afford 1.9 gdesired product (not clean) and 650 mg of cleaner product was obtained from the DCM concentrate.A mixture of above product (1.9 g, 11 mmol), 3-bromo-6-fluoro-imidazo[1,2-b]pyridazine (650mg, 3 mmol), and triethylamine (1.5 ml) in isopropyl alcohol (8 ml) was heated in a microwave at5 140C for 20 min. twice. The reaction mixture was concentrated and the residue was subjected toISCO (40 g column), to gave the titled compound (345 mg). LRMS (ESI) mjz 368 and 370.2 [(M+H)]+,calc’d for C14H1sBrN502: 368.24.B

As the paragraph descriping shows that 95530-58-8 is playing an increasingly important role.

Reference£º
Patent; LEXICON PHARMACEUTICALS, INC.; BI, Yingzhi; CARSON, Kenneth Gordon; CIANCHETTA, Giovanni; GREEN, Michael Alan; KUMI, Godwin; LIANG, Zhi; LIU, Ying Jade; MAIN, Alan; ZHANG, Yulian; ZIPP, Glenn Gregory; WO2013/134219; (2013); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem