The synthetic route of 99395-88-7 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.99395-88-7,(S)-4-Phenyloxazolidin-2-one,as a common compound, the synthetic route is as follows.
4.1.23 (4S,2E)-3-(4′-Methylpent-2′-enoyl)-4-phenyloxazolidin-2-one 4243,44 Butyllithium (1.60 M in hexanes, 8.24 mL, 20.6 mmol) was added slowly via syringe to a stirring solution of (4S)-4-phenyl-2-oxazolidinone 41 (3.37 g, 20.6 mmol) in THF (30 mL) under an atmosphere of nitrogen at -78 C. The resulting solution was stirred for 20 min at -78 C. A solution of (E)-4-methylpent-2-enoylchloride 40 (3.01 g, 22.8 mmol) in THF (17 mL) was added slowly by syringe. The temperature was maintained at -78 C for 30 min at which stage it was raised to 0 C and the reaction mixture stirred at this temperature for 1.5 h. The reaction mixture was then quenched by the addition of saturated aqueous ammonium chloride (30 mL) and the volatiles were removed under reduced pressure. Ethyl acetate (65 mL) was added, the organic phase separated and washed with saturated aqueous sodium bicarbonate (2*30 mL), brine (30 mL), dried and the solvent removed under reduced pressure to give the crude oxazolidinone 42. Purification by flash chromatography on silica gel eluting with ethyl acetate/hexane (20:80) gave the pure oxazolidinone 42 (4.71 g, 88%) as a white solid: mp 100-102 C (lit., 43 103-104 C); [alpha]D20 +105.8 (c 1.0, CHCl3) {lit., 43 [alpha]D20 +103.1 (c 1.0, CHCl3)}; numax/cm-1 (KBr) 2966, 1778, 1685, 1639; deltaH (300 MHz, CDCl3) 1.06, 1.07 [6H, 2* d, 2* J 6.9, CH(CH3)2], 2.42-2.63 [1H, sym m, CH(CH3)2], 4.27 [1H, dd, A of ABX, J 8.7, 3.9, one of C(5)H2], 4.69 [1H, dd appears as t, B of ABX, J 8.7, one of C(5)H2], 5.49 [1H, dd, X of ABX, J 8.7, 3.9, C(4)H], 7.05 [1H, dd, J 15.3, 6.6, C(3′)H], 7.16-7.46 {6H, m, containing 7.22 [1H, dd, J 15.3, 1.2, C(2′)H], ArH}; deltaC (75.5 MHz, CDCl3) 21.1, 21.2 [2* CH3, CH(CH3)2], 31.4 [CH, CH(CH3)2], 57.7 [CH, C(4)H], 69.9 [CH2, C(5)H2], 117.6 [CH, C(2′)H], 125.9, 128.6, 129.1 (3* CH, aromatic CH), 139.1 (C, quaternary aromatic C), 153.7 (C, C=O), 158.1 [CH, C(3′)H], 164.9 (C, C=O)., 99395-88-7
The synthetic route of 99395-88-7 has been constantly updated, and we look forward to future research findings.
Reference£º
Article; Foley, David A.; O’Leary, Patrick; Buckley, N. Rachael; Lawrence, Simon E.; Maguire, Anita R.; Tetrahedron; vol. 69; 6; (2013); p. 1778 – 1794;,
Oxazolidine – Wikipedia
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