99395-88-7, (S)-4-Phenyloxazolidin-2-one is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated
[0728] To a solution of 2-(1-(tert-butoxycarbonyl)-3-vinylazetidin-3-yl)acetic acid (40-3, 1.9 g, 8.12 mmol) in anhydrous THF (30 mL) and cooled to -15 oC was added triethylamine (1.2 mL, 8.93 mmol), followed by dropwise addition of pivaloyl chloride (1.04 mL, 8.52 mmol). The heterogeneous mixture was stirred for 20 min at 0 oC, then re-cooled to -78 oC and stirred for 15 min (solution 1). In a separate flask, (S)-(+)-4-phenyl-2-oxazolidinone (1.32 g, 8.12 mmol) was dissolved in anhydrous THF (30 mL) and cooled to -78 oC. A solution of n-butyl lithium (2.5 M in hexane, 3.2 mL, 8.12 mmol) was added dropwise followed by dropwise addition (15 min) of the mixed anhydride solution (solution 1). The resulting mixture was further stirred for 10 min at -78 oC at which time it was warmed to 0 oC and stirred for 40 min. The reaction mixture was quenched with 10% citric acid (13 mL) and extracted with ethyl acetate (120 mL x 2). The combined organic layers were washed with brine (50 mL x 3), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude residue was purified by CombiFlash column chromatography on silica gel (0- 40% EtOAc in hexane) to afford (S)-4-phenyl-3-(2-(1- (tert-butoxycarbonyl)-3-vinylazetidine-3-yl)acetyl)oxazolidin-2-one (40-4, 2.7 g, 87% yield) as white solid.1H NMR (250 MHz, CDCl3) delta ppm 1.41 (s, 9 H), 3.45 (s, 2 H), 3.77 (t, J = 10.71 Hz, 1 H), 3.82 – 3.93 (m, 2 H), 4.29 (dd, J = 8.90, 3.74 Hz, 1 H), 4.70 (t, J = 8.84 Hz, 1 H), 4.95 – 5.12 (m, 2 H), 5.40 (dd, J = 8.62, 3.57 Hz, 1 H), 6.03 (dd, J = 17.41, 10.71 Hz, 1 H), 7.24 – 7.44 (m, 5 H). MS: [M+H]+ = 386.6.
99395-88-7, As the paragraph descriping shows that 99395-88-7 is playing an increasingly important role.
Reference£º
Patent; ACHAOGEN, INC.; COHEN, Frederick; KONRADI, Andrei W.; CHOI, Taylor Ann Joo; MACHAJEWSKI, Timothy D.; KANE, Timothy Robert; HILDEBRANDT, Darin James; (351 pag.)WO2017/223349; (2017); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem