Acetic Acid → 6-(((1-(2-(tert-butoxy)-2-oxoethyl)-1H-imidazol-2-yl)methyl)(4-(prop-2-yn-1-yloxy)benzyl)amino)hexanoic acid

Participants

Reaction Conditions

Reaction Steps

A solution of 6-((4-(prop-2-yn-1-yloxy)benzyl)amino)hexanoic acid (0.4125 g, 1.50 mmol), tert-butyl 2-(2-formyl-1H-imidazol-1-yl)acetate (0.315 g, 1.50 mmol) and AcOH (0.05 mL) in DCE (40 mL) at 0° C. was treated with NaBH(OAc)3 (0.636 g, 3.0 mmol). The reaction mixture was stirred at 0° C. for 30 min and at room temperature for overnight and decomposed with water and methanol. The reaction mixture was concentrated under reduced pressure to give a residue, which was purified by Biotage SP4 over silica gel to afford 6-(((1-(2-(tert-butoxy)-2-oxoethyl)-1H-imidazol-2-yl)methyl)(4-(prop-2-yn-1-yloxy)benzyl)amino)hexanoic acid (0.268 g, 38%). MS (ESI), 470.3 (M+H)+.

Provenance & Evidence