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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