(3-(((tert-Butoxycarbonyl)amino)(phenyl)methyl)phenoxy)acetic acid → Tert-butyl((3-((3-(4-((1,3-dioxolan-2-yl)methyl)phenyl)-1,2,4-oxadiazol-5-yl)methoxy)phenyl)(phenyl)methyl)carbamate

Participants

Reaction Steps

To a stirred solution of 4-((1,3-dioxolan-2-yl)methyl)-N′-hydroxybenzimidamide (0.747 g, 3.35 mmol) and 2-(3-(((tert-butoxycarbonyl)amino)(phenyl)methyl)phenoxy)-acetic acid (Example 59 Step 2, 1.0 g, 2.79 mmol)) in acetonitrile (5 mL), was added 1-ethyl-3-(3-dimethyllaminopropyl)carbodiimide hydrochloride (0.8 g, 4.18 mmol). The reaction mixture was stirred at ambient temperature for 16 hours. The reaction mixture was diluted with pyridine (1 mL) and heated at 150° C. for 30 minutes in a microwave. The reaction was diluted with saturated brine and extracted with ethyl acetate (×3). The combined organic fractions were dried with magnesium sulphate, and the solvent evaporated at reduced pressure. Material used directly in the next step without further purification (1.01 g, 65%).

Provenance & Evidence