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