Acetic Acid → 3-(2-{6-methyl-2-oxo-3-[(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-ylmethyl)-amino]-2H-pyridin-1-yl}-acetylamino)-3(S)-pyridin-3-yl-propionic acid ethyl ester

Participants

Reaction Steps

To a solution of the amine 16-6 (155 mg, 0.433 mmol), the aldehyde 14-3 (70 mg, 0.433 mmol) in CH2ClCH2Cl was added crushed 4 Å seives, AcOH (20 μL) and then NaB(OAc)3H (184 mg, 0.866 mmol). After stirring for 48 hours, the mixture was filtered through celite, poured into EtOAc and washed with saturated NaHCO3 then brine. The dried (MgSO4) solution was concentrated in vacuo to give a foam type solid. Column chromatography (5% MeOH in CHCl3) afforded the title compound 16-7 as a foam type solid.

Provenance & Evidence