2-Dimethylaminopyridine → N,beta,beta-trimethyl-L-phenylalanyl-N1-((1R,2E)-4-{[4-(benzyloxy)benzyl]oxy}-1-isopropyl-3-methyl-4-oxobut-2-enyl)-N1,3-dimethyl-L-valinamide

Participants

Reaction Steps

A mixture of N,β,β-trimethyl-L-phenylalanyl-N1-[(1S,2E)-3-carboxy-1-isopropylbut-2-enyl]-N1,3-dimethyl-L-valinamide (287 mg, 0.607 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimine hydrochloride (0.728 mmol), 4-(benzyloxy)benzyl alcohol (137 mg, 0.638 mmol) and dimethylaminopyridine (0.12 mmol) in anhydrous dichloromethane (12 mL) are stirred under a nitrogen atmosphere at room temperature for 20 hours. The solvent is removed, the residue taken up in methanol, and the product purified by reverse phase HPLC (0.01% trifluoroacetic acid in water/acetonitrile) to give the title compound as a white gum, 208 mg, MS: m/z 670.4 (M+1).

Provenance & Evidence