ethyl 2-bromo-2-ethylbutanoate

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1-(4-tert-butyl-benzyl)-4-[3-(4-hydroxy-phenyl)-propyl]-3-methyl-imidazolidin-2-one (0.077 g, 0.202 mmol), potassium tert-butoxide (0.091 g, 0.745 mmol) and ethyl α-bromodiethylacetate (0.361 g, 1.61 mmol) in 2-methyl-2-propanol (8 mL) was heated to 100° C. under N2 for 16 h. Aqueous 5 N NaOH (1.5 mL) was added to the reaction mixture and it was heated at reflux an additional 1 h. The reaction mixture was cooled and quenched with 1 N HCl. The mixture was then diluted with water and extracted with CH2Cl2. The organic layer was dried (Na2SO4) and the solvent removed in vacuo to afford 0.288 g of crude product that was purified by preparative HPLC to give 0.014 g (14%) 2-(4-{3-[1-(4-tert-butyl-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-propyl}-phenoxy)-2-ethyl-butyric acid. 1H NMR. HRMS (ES+) m/z exact mass calcd for C30H43N2O4 [M+1] 495.3223, found 495.3252. was heated at reflux an additional 1 h The reaction mixture was cooled quenched with 1 N HCl The mixture was then diluted with water extracted with CH2Cl2 The organic layer was dried (Na2SO4) the solvent removed in vacuo to afford 0.288 g of crude product that was purified by preparative HPLC