p-Toluenesulfonic acid → (R)-methyl-2-(4-nitro-1H-imidazol-1-yl)-octanoate

Participants

Reaction Steps

(R)-2-(4-nitro-1H-imidazol-1-yl)-octanoic acid (16.0 g, 63.0 mmol) was dissolved in 1 L of anhydrous methanol. To this solution was added pTsOH (300 mg). The reaction was then heated to reflux for 16 hours. Upon cooling, the solvent was removed in vacuo, to give an oil that was dissolved in 300 mL of ethyl acetate. The solution was washed (2×250 mL) with saturated NaHCO3 solution The organic was then dried (Na2SO4) and concentrated in vacuo to provide 13.2 g (78%) of (R)-methyl-2-(4-nitro-1H-imidazol-1-yl)-octanoate as an amber oil.

Provenance & Evidence