反应详情

A solution of 2-methyl-3-{4-[2-(3-methyl-2-oxo-imidazolidin-4-yl)-ethoxy]-phenyl}-2-phenoxy-propionic acid ethyl ester (0.109 g, 0.255 mmol) in DMF (7 mL) is treated with NaH (60% oil suspension, 0.021 g, 0.525 mmol) and stirred at room temperature under N2 for 20 minutes. The reaction is treated with 2-trifluoromethyl benzyl bromide (0.092 g, 0.385 mmol) and then warmed to room temperature and stirred for 3 hours. The reaction is quenched with acid and worked up extractively with Et2O and water. The organic layer is dried and the solvent removed to afford crude product that is dissolved in ethanol (20 mL) is treated with aqueous 5 N NaOH (1.5 mL) and heated to reflux 1 hour. The reaction mixture is cooled, the solvent removed. The resultant residue is acidified with aqueous 1 N HCl (20 mL) and extracted with CH2Cl2. The organic layer is dried and the solvent removed in vacuo to afford crude acid that is purified by preparative HPLC to give 0.096 g (68%) of 2-methyl-3-(4-{2-[3-methyl-2-oxo-1-(2-trifluoromethyl-benzyl)-imidazolidin-4-yl]-ethoxy}-phenyl)-2-phenoxy-propionic acid 1H NMR. HRMS (ES+) m/z exact mass calc'd for C30H32N2O5F3 (M+1) 557.2263. Found m/z 557.2274.

1. temperaturewarmed to room temperature
2. stirringstirred for 3 hours
3. customThe reaction is quenched with acid
4. customThe organic layer is dried
5. customthe solvent removed
6. customto afford crude product that
7. temperatureheated
8. temperatureto reflux 1 hour
9. temperatureThe reaction mixture is cooled
10. customthe solvent removed
11. extractionextracted with CH2Cl2
12. customThe organic layer is dried
13. customthe solvent removed in vacuo
14. customto afford crude acid that
15. customis purified by preparative HPLC