Tag: 131685-53-5

131685-53-5, (R)-(-)-4-Benzyl-3-propionyl-2-oxazolidinone is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

(76a) (S)-4-Benzyl-3-[(2R,4E)-6-benzyloxy-2-methylhex-4-enoyl]oxazolidin-2-one 164 ml of a solution of sodium bis(trimethylsilyl)amide in n-hexane (1.03 mol/l) (169 mmol) was added to a solution of 32.9 g of (S)-4-benzyl-3-propionyloxazolidin-2-one (141 mmol) in tetrahydrofuran (330 ml) under a nitrogen atmosphere and at -78C over 45 minutes, and the mixture was stirred at the same temperature for 30 minutes. Then, a solution of 35.5 g of [(E)-4-bromobut-2-enyloxymethyl]benzene obtained in Reference Example 4 (148 mmol) in tetrahydrofuran (80 ml) was added to the solution over 30 minutes, and the mixture was stirred at the same temperature for 30 minutes. Thereafter, the mixture was raised to -40C and further stirred for four hours. 100 ml of a saturated ammonium chloride aqueous solution was added to the reaction mixture, and the mixture was further stirred at room temperature for one hour. The reaction mixture was concentrated under reduced pressure and diluted with 500 ml of water, followed by extraction with ethyl acetate. Then, the organic layer was washed with water and brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (elution solvent: n-hexane/ethyl acetate = 7/1 – 2/1) to obtain 37.9 g of the title compound (yield: 69%). Colorless liquid. 1H NMR spectrum (CDCl3, 400 MHz), delta: 7.40-7.14 (m, 10H), 5.75 (dt, 1H, J = 15.6 Hz, 6.3 Hz), 5.69 (dt, 1H, J = 15.6 Hz, 5.4 Hz), 4.71-4.63 (m, 1H), 4.49 (s, 2H), 4.22-4.11 (m, 2H), 3.98 (d, 2H, J = 5.5 Hz), 3.92-3.81 (m, 1H), 3.28 (dd, 1H, J = 13.3 Hz, 3.1 Hz), 2.67 (dd, 1H, J = 13.3 Hz, 10.2 Hz), 2.58-2.49 (m, 1H), 2.30-2.21 (m, 1H) 1.19 (d, 3H, J = 6.7 Hz).

131685-53-5, The synthetic route of 131685-53-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Daiichi Sankyo Company, Limited; EP2036896; (2009); 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.131685-53-5,(R)-(-)-4-Benzyl-3-propionyl-2-oxazolidinone,as a common compound, the synthetic route is as follows.

To a solution of (+)-(S)-4-benzyl-3-propyl-2-oxazolidinone (3.00 g, 12.9 mmol) in DCM (70.0 mL) was added 1.0 M dibutylboron triflate in DCM (14.2 mL, 14.2 mmol) and Et3N (2.69 mL, 19.3 mmol) at -78 oC, and then stirring was continued for 30 min at -40 oC. To the reaction mixture cooled to -78 oC was added a solution of 4-benzyloxy-3-methoxybenzaldehyde (3.40 g, 14.2 mmol) in DCM (60.0 mL). After stirring for 11 h, the reaction was quenched by addition of phosphoric buffer (15.4 mL), methanol (51.5 mL), and 30% H2O2 (15.4 mL) at 0 oC. The mixture was stirred for 1 h. The aqueous layer was extracted with DCM and the combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography (hexane:AcOEt = 2:1) to afford 5 (4.88 g, 80%, 98% de) as colorless solid: 1H NMR (400 MHz, CDCl3) delta 7.40-7.43 (2H, m), 7.24-7.35 (6H, m), 7.17-7.19 (2H, m), 6.92 (1H, d, J = 1.7 Hz), 6.83 (1H, d, J = 8.0 Hz), 6.80 (1H, dd, J = 8.0, 1.7 Hz), 5.14 (2H, s), 4.97 (1H, d, J = 4.7 Hz), 4.49 (1H, dddd, J = 9.6, 8.4, 3.4, 2.4 Hz), 4.11 (1H, qd, J = 6.8, 4.7 Hz), 4.08 (1H, dd, J = 9.0, 2.4 Hz), 3.94 (1H, dd, J = 9.0, 8.4 Hz), 3.86 (3H, s), 3.22 (1H, dd, J = 13.3, 3.4 Hz), 2.74 (1H, dd, J = 13.3, 9.6 Hz), 1.25 (3H, d, J = 6.8 Hz); 13C NMR (100 MHz, CDCl3) delta 176.5, 152.9, 149.5, 147.4, 137.1, 135.0, 134.5, 129.4, 129.0, 128.5, 127.8, 127.4, 127.3, 118.3, 113.5, 109.7, 74.0, 70.9, 66.1, 56.0, 55.3, 44.6, 37.8, 11.4; IR (ATR) 3509, 1775, 1695 cm-1; EIMS (rel. int.) m/z 475 [M]+(1), 91 (100); HREIMS calcd 475.1995 for C28H29O6N, found 475.1979; [alpha]D20 +58.9 (c 1.00, CHCl3); m.p. 117.0 oC., 131685-53-5

As the paragraph descriping shows that 131685-53-5 is playing an increasingly important role.

Reference£º
Article; Harada, Kenichi; Horiuchi, Hiroki; Tanabe, Kazuma; Carter, Rich G.; Esumi, Tomoyuki; Kubo, Miwa; Hioki, Hideaki; Fukuyama, Yoshiyasu; Tetrahedron Letters; vol. 52; 23; (2011); p. 3005 – 3008;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.131685-53-5,(R)-(-)-4-Benzyl-3-propionyl-2-oxazolidinone,as a common compound, the synthetic route is as follows.

131685-53-5, A solution of oxazolidinone (+)-1a (1.79 g, 7.67 mmol) in degassed CH2CI2 (30 mL, 4 A MS dried, argon sparged) was cooled to 0 C and n-Bu2BOTf (1.0 M in hexane, 7.67 mL) was introduced, followed by addition of NiPr2Et (1.34 mL, 8.05 mmol). The mixture was cooled to-78 C. A precooled (- 78 C, degassed solution of aldehyde (+) -1 (2.2 g, 6.66 mmol) in CH2CI2 (8 mL) was then added via cannula over 0.25 h (2 mL rinse). After an additional 1.0 h at-78 C, the reaction was warmed to-0 C, stirred for 1 h, then quenched with pH 7 potassium phosphate monobasic-sodium hydroxide buffer (0.05 M, 5.5 mL). A solution of 30% H2O2 in MeOH (1: 2,17 mL) was added to the vigorously stirred reaction mixture at such a rate as to maintain an internal temp < 8 C (15 min, 0'C cooling bath). The reaction was stirred 1 h at room temperature, and the resulting layers were separated. The aqueous layer was extracted (3 x CH2CI2), and the combined organic layers were washed with saturated aqueous NaHCO3 (15 mL), water (15 mL) and saturated brine (2 x 10 mL). The organic layer was dried over MgS04, filtered, and concentrated in vacuo. Flash chromatography (20% ethyl acetate/hexanes) provided (+)-2 (3. 4 9, 85%) as a white foam. [a] 2D +17. 0 (c = 1, CHCI3) ; IR (NaCI) 3523,3081, 3052,2971, 2925, 2872, 1780,1699, 1489,1447, 1157,1099, 1070 ; 1H NMR (500 MHz, CDCI3) 8 7.48 (m, 6H), 7.37-7. 29 (m, 8H), 7.28-7. 20 (m, 6H), 4.67 (dddd, J = 8.9, 5.6, 5.2, 3.7 Hz, 1H), 4.17 (d, J = 5.2 Hz, 2H), 4.04 (ddd, J = 5.9, 4.8, 3.3 Hz, 1H), 3.92 (dddd, J = 6.7, 6.7, 6.7, 6.7 Hz, 1H), 3.25 (dd, J = 13.4, 3.4 Hz, 1H), 3.23 (dd, J= 9.3, 5.6 Hz, 1H), 3.17 (dd, J= 9.3, 5.2 Hz, 1H), 2.96 (d, J= 3.35 Hz, 1H), 2.78 (dd, J= 13.4, 9.7 Hz, 1H), 1.89 (m, 1H), 1.32 (d, J = 6. 7 Hz, 3H), 1.09 (d, J = 6. 7 Hz, 3H) ; 13C NMR (125 MHz, CDCI3) 6 176.8, 152.6, 143.9, 135.1, 129.4, 128.9, 128.6, 127.8, 127.4, 126.9, 86.9, 73.8, 67.0, 66.0, 55.1, 40.8, 37.7, 36.5, 13.2, 12.2 ; high resolution mass spectrum (ES+) m/z 586.2561, [ (M) +, calcd for C36H37NOsNa : 586.2569]. The synthetic route of 131685-53-5 has been constantly updated, and we look forward to future research findings. Reference£º
Patent; THE TRUSTEES OF THE UNIVERSITY OF PENNSYLVANIA; WO2005/35489; (2005); A2;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

131685-53-5, (R)-(-)-4-Benzyl-3-propionyl-2-oxazolidinone is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,131685-53-5

To a solution of 16a (22.4 g, 96.0 mmol) in THF (300 mL) cooled to -78 C was added NaHMDS (100 mL, 100 mmol, 1.0 M solution in THF) dropwise over 20 min. The reaction was stirred at -78 C for an additional hour before the dropwise addition of allyl iodide (8.78 mL, 96.0 mmol) over 10 min. The reaction was stirred for an additional 5 hr at -78 C before the cooling bath was removed and the reaction was quenched with the addition of sat. NH4Cl. The layers were separated, and the aqueous layer was washed with Et2O x 3. The combined organic material was washed with sat. Na2S2O3, dried over MgSO4, filtered, concentrated, and purified via flash chromatography (Teledyne ISCO flash chromatography system; silica gel column; 9:1Hexane:EtOAc) to afford the desired product as a colorless oil (14.9 g, 58% yield). Spectral data were in accordance with reported literature values.5

The synthetic route of 131685-53-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Reed, Carson W.; Fulton, Mark G.; Nance, Kellie D.; Lindsley, Craig W.; Tetrahedron Letters; vol. 60; 10; (2019); p. 743 – 745;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.131685-53-5,(R)-(-)-4-Benzyl-3-propionyl-2-oxazolidinone,as a common compound, the synthetic route is as follows.

To a flame dried 250 mL round bottom flask equipped with a stir bar was added oxazolidinone A (7.0g, 30 mmol) and ethyl acetate (100 mL). To the stirred solution was added MgCl2 (570 mg, 6 mmol), triethylamine (5.7 mL, 45 mmol), and benzaldehyde (3.66 mL, 36 mmol). The reaction was stirred over night then the yellow solution was filtered through a plug of silica (5 cm x 5 cm) with diethyl ether (500 mL). The volatiles were removed in vacuo followed by the addition of methanol (50 mL) and 3 drops of trifluoroacetic acid. The solution was stirred for 1 h; a white precipitate formed, was filtered and washed with methanol (50 mL). The white solid was dried to obtain 8.28 g (81%).

131685-53-5 (R)-(-)-4-Benzyl-3-propionyl-2-oxazolidinone 10966403, aoxazolidine compound, is more and more widely used in various.

Reference£º
Article; Dixon, Alexandre D.C.; Wilson, Robert J.; Nguyen, Daniel D.; Clark, Daniel A.; Tetrahedron Letters; vol. 58; 43; (2017); p. 4054 – 4056;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem