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.
The compound was synthesized as trifluoroacetate salt starting from (S)-4-phenyloxazolidin-2-one (1 equiv., 0.163 g, 1 mmol), 4-iodobenzene-1,2-diamine (1 equiv., 0.234 g, 1 mmol), copper(I) iodide (0.1 equiv., 0.019 g, 0.1 mmol), cesium fluoride (2 equiv., 0.304 g, 2 mmol), cyclohexane-1,2-diamine (0.1 equiv., 0.012 mL, 0.1 mmol). The solids were given together in a reaction flask and the flask was purged with argon. A solution of cyclohexane-1,2-diamine in 4 mL dioxane was added to the flask. The reaction was stirred at 95 C. for 20 hours, before the reaction was cooled down to 45 C. and filtered through a pad of celite. The pad was washed with warm dichloromethane and the solution was concentrated under reduced pressure. The intermediate product was purified via FPLC using a chloroform-methanol gradient (0?10%, product elutes at about 5%). Yield: 0.215 g (80%); MS m/z 270.3 (M+H)+ The (S)-3-(3,4-diaminophenyl)-4-phenyloxazolidin-2-one was dissolved in 12 mL of triethyl orthoacetate and the reaction was stirred at 150 C. for 0.5 h before the reaction was cooled down. The excess of triethyl orthoacetate was removed under reduced pressure. The final product was purified by means of FPLC using chloroform-methanol gradient (0?10%), followed by preparative HPLC using a water-acetonitrile gradient with 0.04% trifluoroacetic acid.Yield: 0.095 g (23.3%); MS m/z 294.2 (M+H)+; 1H NMR (400 MHz, DMSO-D6): delta 2.67 (s, 3H); 4.16-4.20 (m, H); 4.85-4.89 (m, H); 5.79-5.83 (m, H); 7.24-7.40 (m, 5H); 7.49 (dd, H, 3J=9.1 Hz, 4J=2.1 Hz); 7.63 (d, H, 3J=9.1 Hz); 7.76 (d, H, 4J=2.1 Hz), HPLC (lambda=214 nm), [B]: rt 8.69 min (100%)., 99395-88-7
99395-88-7 (S)-4-Phenyloxazolidin-2-one 730424, aoxazolidine compound, is more and more widely used in various fields.
Reference£º
Patent; PROBIODRUG AG; US2011/92501; (2011); A1;,
Oxazolidine – Wikipedia
Oxazolidine | C3H7NO – PubChem