Methyl 1-bromocyclohexanecarboxylate → HCID 57718925, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-(4-tert-butyl-benzyl)-4-[3-(4-hydroxy-phenyl)-propyl]-3-methyl-imidazolidin-2-one (0.074 g, 0.194 mmol) and potassium tert-butoxide (0.044 g, 0.392 nmol) in 2-methyl-2-propanol (8 mL) was heated to 60° C. under N2 and then and methyl 1-bromocyclohexanecarboxylate (0.274 g, 1.16 mmol) was added dropwise to the to 60° C. solution. Additional potassium tert-butoxide (0.044 g, 0.392 mmol) and methyl 1-bromocyclohexanecarboxylate (0.274 g, 1.16 mmol) was added to the reaction and it was stirred for 2 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 0.400 g of crude product that was purified by preparative HPLC to give 0.059 g (60%) 1-(4-{3-[1-(4-tert-butyl-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-propyl}-phenoxy)-cyclohexanecarboxylic acid. 1H NMR. HRMS (ES+) m/z exact mass calcd for C31H43N2O4 [M+1] 507.3223, found 507.3237.

Provenance & Evidence