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.
A solution of sodium bis(trimethylsilyl)amide in n-hexane (1.03 M, 164 mL, 169 mmol) was added to a solution of 11c (32.9 g, 141 mmol) in THF (330 mL) under N2 atmosphere and at -78 C over 45 min, and the mixture was stirred at the same temperature for 30 min. Then, a solution of benzyl (2E)-4-bromobut-2-en-1-yl ether (35.5 g, 148 mmol) in THF (80 mL) was added to the above solution over 30 min, and the mixture was stirred at the same temperature for 30 min. The reaction mixture was raised to -40 C and further stirred for 4 h. Saturated NH4Cl aqueous solution (100 mL) was added to the reaction mixture, and the mixture was further stirred at room temperature for 1 h. The reaction mixture was concentrated under reduced pressure and diluted with water (500 mL), followed by extraction with AcOEt. Then, the organic layer was washed with water and brine, and dried over anhydrous MgSO4. After filtration, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent, n-hexane/AcOEt = 7:1-2:1) to obtain (4S)-4-benzyl-3-[(2R,4E)-6-(benzyloxy)-2-methylhex-4-enoyl]-1,3-oxazolidin-2-one (37.9 g, 69%, 99% ee) as a colorless liquid. 1H NMR (400 MHz, CDCl3): delta 7.40-7.14 (m, 10H), 5.75 (dt, 1H, J = 15.6, 6.3 Hz), 5.69 (dt, 1H, J = 15.6, 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, 3.1 Hz), 2.67 (dd, 1H, J = 13.3, 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
131685-53-5 (R)-(-)-4-Benzyl-3-propionyl-2-oxazolidinone 10966403, aoxazolidine compound, is more and more widely used in various fields.
Reference£º
Article; Nakamura, Yuji; Fujimoto, Teppei; Ogawa, Yasuyuki; Namiki, Hidenori; Suzuki, Sayaka; Asano, Masayoshi; Sugita, Chie; Mochizuki, Akiyoshi; Miyazaki, Shojiro; Tamaki, Kazuhiko; Nagai, Yoko; Inoue, Shin-Ichi; Nagayama, Takahiro; Kato, Mikio; Chiba, Katsuyoshi; Takasuna, Kiyoshi; Nishi, Takahide; Bioorganic and Medicinal Chemistry; vol. 21; 11; (2013); p. 3175 – 3196;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem