Acetic Acid → Ethyl pentanimidate hydrochloride

Participants

Reaction Conditions

Reaction Steps

A mixture of 35 mg (0.0484 mmole) of 5-n-butyl-2,4-dihydro-2-[2-(hydroxymethyl)phenyl]-4-[[2'-(N-trityltetrazol-5-yl)biphenyl-4-yl]methyl]-3H-1,2,4-triazol-3-one, 0.5 mL of glacial acetic acid, and 0.25 mL of H2O was stirred at 60° C. overnight, TLC in 90:10 CH2Cl2 --MeOH showed two products at Rf <0.25. After cooling to room temperature, solvents were evaporated and the residue flash chromatographed over silica gel (gradient elution with 4-10% methanol in CH2Cl2) to give 7 mg of product B (the acetate) as an oil and 12 mg of product A (the hydroxy compound) as a clear oil. Each compound was homogeneous by TLC in 90:10 CH2Cl2 --MeOH, mass spectrum (FAB) for A m/e 482 (M+1)+ and for B m/e 524(M+1)+.

Provenance & Evidence