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