95530-58-8 -| Page 2 of 2 | Heterocyclic Building Blocks-Oxazolidine

Simple exploration of 95530-58-8

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

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, General procedure: Pivaloyl chloride (0.684 mL, 5.69 mmol) was added, over 30 min, into a mixture of compound 6 (2.117 g, 5.42 mmol) and triethylamine (0.907 mL, 6.51 mmol) in dry tetrahydrofuran (50 mL) at -78 C. Sequentially, the resulting solution was stirred at 0 C for 30 min and recooled to -78 C. A -78 C solution of lithium (R)-4-isopropyl-2-oxooxazolidin-3-ide (prepared from (R)-4-isopropyloxazolidin-2-one (0.770 g, 5.96 mmol) and nBuLi (3.73 mL 1.6 M/hexane, 5.96 mmol) in THF at -78 C) was transferred through a cannula to the mixture above. Then the resulting mixture was warmed to room temperature. After another 30 min stirring, the reaction was quenched with a saturated NH4Cl aqueous (100 mL), and then extracted with ethyl acetate (100 mL). Organic layer was washed with brine and dried over anhydrous Na2SO4. The organic solution was concentrated and the residue was over silica gel column eluting with petroleum ether/ethyl acetate (2:1) to give compound (R)-7 (2.268 g, 83.4%) as a yellow oil; 1H NMR (300 MHz, CDCl3) delta 7.99-7.96 (m, 2H, ArH), 7.50 (s, 1H, ArH), 7.43-7.40 (m, 3H, ArH), 7.36 (d, 1H, ArH, J = 8.7 Hz), 7.16 (d, 1H, ArH, J = 8.7 Hz), 4.43-4.38 (m, 1H, CH), 4.27-4.16 (m, 2H, CH2), 3.36-3.17 (m, 2H, CH2), 3.07 (t, 2H, CH2, J = 6.8 Hz), 2.96 (t, 2H, CH2, J = 7.4 Hz), 2.63 (t, 2H, CH2, J = 7.2 Hz), 2.37-2.22 (m, 2H, CH2), 2.30 (s, 3H, CH3), 0.89 (d, 3H, CH3, J = 7.5 Hz), 0.82 (d, 3H, CH3, J = 6.9 Hz); HRMS-ESI+: C29H31N3O5 calcd [M + H]+ 502.2342, found 502.2359.

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

Reference£º
Article; Zhang, Wei; Liu, Wenlu; Jiang, Xizhen; Jiang, Faqin; Zhuang, Hao; Fu, Lei; European Journal of Medicinal Chemistry; vol. 46; 9; (2011); p. 3639 – 3650;,
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New learning discoveries about 95530-58-8

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

95530-58-8,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.

caproyl chloride is reacted with the Evans valine-derived oxazolidinone, (R)-4-isopropyloxazolidin-2-one, and n-butylLi (Step a). The resulting adduct (2) is reacted by aldol condensation with a chiral aldehyde derived from (S)-(-)-lactic acid (3) in the presence of dibutyl-BOTf and triethylamine (Step b). The 4-hydroxyl group of the resulting adduct (4) is protected as a t-butyldimethylsilyl ether (using TBS chloride and DIEA), followed by peroxide-mediated hydrolysis (using hydrogen peroxide and lithium hydroxide) of the chiral auxiliary to yield the differentially protected dihydroxy pentanoic acid (5) (Steps c and d). Differential protection of the two secondary alcohols allows for the incorporation of various carboxylic acids at the 3 position of the lactone. The carboxylic acid is coupled to N-FMOC-L-threonine benzyl ester with BOP-chloride and DMAP (Step e). Removal of the two benzyl protecting groups with H2 and Pd/O will yield the dilactone seco-acid (6) (Step f). Lactonization occurs using a BOP-Cl mediated ester-forming reaction with DMAP (Step g). Diethylamine is used to remove the FMOC protecting group to yield the dilactone (7) (Step h). N-formyl-3-amine salicylic acid is coupled to the dilactone using standard carbodiimide chemistry (Step i). In particular, the dilactone is combined with N-formyl-3-aminosalicylic acid using EDCl and HOBT, followed by treatment with TBAF. The final elaboration of the derivatized antimycin A3 structure is accomplished by fluoride-mediated removal of the silyl protecting group and coupling of the desired acid chloride (e.g., isobutyryl chloride and DIEA) (Steps j and k).

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

Reference£º
Patent; Fred Hutchinson Cancer Research Center; US2005/239873; (2005); A1;,
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Simple exploration of 95530-58-8

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

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 flame-dried 100 mL round-bottom flask was added 3,4,5-trimethoxyphenylacetic acid (2.10 g, 9.29 mmol). THF (25 mL) was added followed by Et3N (1.42 mL, 10.22 mmol). The solution was cooled to -78 C. Pivaloyl chloride (1.26 mL, 10.22 mmol) was added dropwise and the solution warmed to 0 C. and stirred for 1 h. In a separate flame-dried 50 mL round-bottom flask was added (R)-4-isopropyloxazolidin-2-one (1.0 g). THF (20 mL) was added and the solution cooled to -78 C. n-BuLi (6.83 mL, 9.29 mmol, 1.36 M) was added dropwise and the solution stirred at -78 C. for 15 min and then warmed to 25 C. where it was stirred for 15 min. The organolithium solution was transferred to the solution of the mixed anhydride via cannula at -78 C. The reaction was stirred at -78 C. for 15 min, warmed to 0 C., and stirred for 1 h. Water (10 mL) was added and the aqueous layer extracted with EtOAc (2*10 mL). The combined organics were washed with brine (10 mL), dried over anhydrous MgSO4, and concentrated under reduced pressure. The residue was purified by flash chromatography (SiO2, 30 g) using 25% EtOAc in hexanes as the eluent to afford trimethoxyphenyl)acetyl)oxazolidin-2-one as a colorless oil (2.30 g, 88%): Rf=0.28 (1:1, Hex:EtOAc); 1H NMR (CDCl3) delta 6.55 (s, 2H), 4.44-4.41 (m, 1H), 4.29-4.24 (m, 2H), 4.19 (dd, J) 9.0, 3.0 Hz, 1H), 4.12-4.07 (m, 1H), 3.82 (s, 6H), 3.80 (s, 3H), 2.36-2.30 (m, 1H), 0.87 (d, J) 6.8 Hz, 3H), 0.78 (d, J) 7.1 Hz, 3H); 13C NMR (CDCl3) delta 171.2, 154.1, 153.2, 129.4, 106.7, 63.4, 60.9, 58.6, 56.2, 41.6, 28.4, 18.0, 14.7, 14.3; HRFAB[M+Li]344.1686 (calculated C17H23NO6Li: 344.1686).

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

Reference£º
Patent; University of Connecticut; US2009/105287; (2009); A1;,
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Oxazolidine | C3H7NO – PubChem

Brief introduction of 95530-58-8

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

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

The R type EvansAuxiliary base addedTo 250 ml of dry reaction flask,70 ml of anhydrous THF dissolved,Cooled to -78 C,And then slowly adding n-BuLi (18.5 ml, 46.3 mmol)After 30 min reaction,(E) -2-methyl-2-butenoyl chloride (5.0 g, 42.5 mmol) was added and reacted for 30 min. The temperature was raised to 0 C and the reaction was continued for 15 min.20ml saturated ammonium chloride quenching reaction, separationThe organic phase was extracted with ethyl acetate (20 ml x 3). The organic phases were combined, washed with saturated brine (40 ml), dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated under reduced pressure.The residue was subjected to column chromatography (elution conditions, petroleum ether: ethyl acetate = 10: 1) to give the product as a white solid, 7.7 g, 94% yield;

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

Reference£º
Patent; Fudan University; Lei Xinsheng; Lin Guoqiang; Zhao Qun; Xu Qianqian; Shan Guangsheng; (20 pag.)CN104418707; (2017); B;,
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New learning discoveries about 95530-58-8

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

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

A 2.5M solution of n-butyllithium in hexanes (34.0mL, 85mmol) was added dropwise at -78C to a solution of (4R)-isopropyloxazolidinone (10.0g, 77mmol) in anhydrous THF (100mL). The mixture was stirred at -78C for 15min, and freshly distilled tiglyl chloride (9.3mL, 85mmol), prepared from tiglic acid and SOCl2, was added dropwise to the mixture. The mixture was stirred for 30minat -78C and slowly warmed up to 0C. After 15minat 0C, the mixture was quenched with a satd NH4Cl aqsolution (20mL). The organic solvents were evaporated and the mixture was extracted with AcOEt (50mL¡Á3). The combined extract was washed with brine (30mL), dried over MgSO4, concentrated, and purified by column chromatography (Petroleum ether/ethyl acetate=10:1). Compound 1 was obtained as a white solid (15.5g, 95%); mp 62-63C. Rf (Petroleum ether/ethyl acetate=10:1) 0.40. [alpha]D20 -91.2 (c 0.13, CHCl3). [lit.:20 its enantiomer, mp 63-64C. [alpha]D30 +91.8 (c 0.07, CHCl3)]. 1H NMR (400MHz, CDCl3) delta 6.21 (q, J=6.8Hz, 1H), 4.58-4.46 (m, 1H), 4.32 (dd, J=8.9, 8.9Hz, 1H), 4.17 (dd, J=8.9, 5.6Hz, 1H), 2.42-2.28 (m, 1H), 1.91 (s, 3H), 1.81 (d, J=8.9Hz, 3H), 0.92 (d, J=7.1Hz, 3H), 0.91 (d, J=6.6Hz, 3H). ESI-MS: Calcdfor C11H18NO3+ [M+H]: 212.1, found:

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

Reference£º
Article; Xu, Qian-Qian; Zhao, Qun; Shan, Guang-Sheng; Yang, Xi-Cheng; Shi, Qi-Yuan; Lei, Xinsheng; Tetrahedron; vol. 69; 50; (2013); p. 10739 – 10746;,
Oxazolidine – Wikipedia
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Simple exploration of 95530-58-8

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

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

The R-type Evans cofactor was added to a 250 ml dry reaction flask and dissolved in 70 ml of dry THF. The solution was cooled to -78 C and n-BuLi (18.5 ml, 46.3 mmol) was added slowly. After 30 min, (E) -2-methyl-2-butyryl chloride (5.0 g, 42.5 mmol) was added and the reaction was allowed to proceed for 30 min and the temperature was raised to 0 C. (20 ml of X3). The combined organic layers were washed with saturated brine (40 ml), dried over anhydrous sulfuric acid (20 ml) and concentrated in vacuo. The organic layer was extracted with ethyl acetate,Dried and filtered. The filtrate was concentrated under reduced pressure and the residue was subjected to column chromatography (elution conditions, petroleum ether: ethyl acetate = 10: 1) to give the product as a white solid (yield: 94%).

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

Reference£º
Patent; Fudan University; Lei, Xinsheng; Lin, Guojiang; Xu, Qianqian; Zhao, Qun; (29 pag.)CN104341276; (2016); B;,
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New learning discoveries about 95530-58-8

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

A mixture of 2-(3-bromo-phenyl)-3,3-dimethyl-l,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 120C for 16 h. Then the reaction mixture cooled to room temperature. The reaction mixture was extracted with ethyl acetate (2 x 150 mL), washed with water (2 x 50 mL) and saturated aqueous ammonium chloride solution (2 x 50 mL), dried over anhydrous sodium sulfate and then concentrated in vacuo. Purification by Waters automated flash system (column: Xterra 30 mm x 100 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- l,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.

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

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; CHEN, Li; FENG, Lichun; HUANG, Mengwei; LIU, Yongfu; WU, Guolong; WU, Jim, Zhen; ZHOU, Mingwei; WO2011/128251; (2011); A1;,
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Some tips on 95530-58-8

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

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).

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

Reference£º
Article; Bello, Jan E.; Millar, Jocelyn G.; Tetrahedron Asymmetry; vol. 24; 13-14; (2013); p. 822 – 826;,
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Analyzing the synthesis route of 95530-58-8

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

A cooled (-20 C) solution of tiglic acid (2.005 g, 20.031 mmol) in anhydrous tetrahydrofuran (50 mL) was sequentially treated with triethylamine (6.1 mL, 44.068 mmol) and dropwise pivaloyl chloride (2.7 mL, 22.034 mmol). After stirring at -20 C for 30 min, lithium chloride (1.019 g, 24.037 mmol) and (R)-(+)-4-isopropyl-2-oxazolidinone (2.587 g, 20.031 mmol) were added. The reaction mixture was allowed to slowly warm to room temperature, stirred for 3 days and was then quenched with saturated ammonium chloride. The aqueous layer was extracted with ethyl acetate (2 x). The organics were combined, dried over anhydrous sodium sulfate, filtered and the volatiles were removed in vacuo. The residue was purified by silica gel chromatography using a 50 g Isolute cartridge eluted with a continuous gradient of iso- hexanes/ethyl acetate 1 :0 to 4:1 to afford the title compound (3.307 g, 78%) as a colourless solid. 1H NMR (300 MHz, CDCl3): delta 0.92 (d, J = 6.9 Hz, 3H), 0.94 (d, J = 7.1 Hz, 3H), 1 .83 (d, J = 6.9 Hz, 3H), 1.93 (s, 3H), 2.38 (d of heptet, J = 6.9, 4.2 Hz, 1 H), 4.19 (dd, J = 8.9, 4.6 Hz, 1 H), 4.33 (app t, J = 8.9 Hz, 1 H), 4.49-4.58 (m, 1 H), 6.23 (q, J = 7.1 Hz, 1 H)

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

Reference£º
Patent; GILEAD SCIENCES, INC.; SELCIA LIMITED; ACIRO, Caroline; STEADMAN, Victoria Alexandra; PETTIT, Simon Neil; POULLENNEC, Karine G.; LAZARIDES, Linos; DEAN, David Kenneth; DUNBAR, Neil Andrew; HIGHTON, Adrian John; KEATS, Andrew John; SIEGEL, Dustin Scott; KARKI, Kapil Kumar; SCHRIER, Adam James; JANSA, Petr; MACKMAN, Richard; WO2013/185103; (2013); A1;,
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