With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.17016-83-0,(S)-4-Isopropyl-2-oxazolidinone,as a common compound, the synthetic route is as follows.
Intermediate S-i H: (4S)-4-(Propan-2-yl)-3 -(5,5,5 -trifluoropentanoyl)- 1,3 -oxazolidin-2- one[00146j To a stirred solution of 5,5,5-trifluoropentanoic acid (5.04 g, 32.3 mmol) in DCM (50 mL) and DMF (3 drops) was added oxalyl chloride (3.4 mL, 38.8 mmol) dropwise over 5 mm and the solution was stirred until all bubbling subsided. The reaction mixture was concentrated under reduced pressure to give pale yellow oil. To a separate flask charged with a solution of (4S)-4-(propan-2-yl)- 1 ,3-oxazolidin-2-one (4.18g, 32.4 mmol) in THF (100 mL) at -78 C was added n-BuLi (2.5M in hexane) (13.0 mL,32.5 mmol) dropwise via syringe over 5 mm. After stirring for 10 mm, the above acid chloride dissolved in THF (20 mL) was added via cannula over 15 mm. The reaction mixture was warmed to 0 C, and was allowed to warm to room temperature as the bath warmed and stirred overnight. To the reaction mixture was added saturated NH4C1, andthen extracted with EtOAc (2x). The combined organics were washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The crude material was purified by flash chromatography (Teledyne ISCO CombiFlash Rf, 5% to 60% solvent A/B=hexanes/EtOAc, REDISEP Si02 1 20g). Concentration of appropriate fractions provided Intermediate S-1H (7.39 g, 86%) as a colorless oil: ?H NMR (400 MHz, CDC13)o ppm 4.44 (1 H, dt, J=8.31, 3.53 Hz), 4.30 (1 H, t, J=8.69 Hz), 4.23 (1 H, dd, J9.06,3.02 Hz), 2.98-3.08 (2 H, m), 2.32-2.44 (1 H, m, J=13.91, 7.02, 7.02, 4.03 Hz), 2.13-2.25(2 H, m), 1.88-2.00 (2 H, m), 0.93 (3 H, d, J=7.05 Hz), 0.88 (3 H, d, J6.80 Hz).
17016-83-0, As the paragraph descriping shows that 17016-83-0 is playing an increasingly important role.
Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; HAN, Wen-Ching; GILL, Patrice; GAVAI, Ashvinikumar, V.; QUESNELLE, Claude, A.; WO2014/47393; (2014); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem