Sodium Hydroxide → HCID 19093675, compound

Participants

Reaction Steps

Ethyl 5,7-diethyl-2-oxo-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)methyl]-1,2-dihydro-1,6-naphthyridin-3-carboxylate (0.41 g) was dissolved in dioxan (5 ml) containing aqueous 1M sodium hydroxide solution (0.55 ml) and the mixture was stirred for 16 hours. Volatile material was removed by evaporation and the residue was partitioned between ethyl acetate and water. The aqueous phase was separated, acidified to pH 4-5 with 1M aqueous citric acid solution and then extracted twice with dichloromethane. The combined extracts were dried (MgSO4) and the solvent was removed by evaporation. The residue was purified by flash chromatography, eluting initially with ethyl acetate/petroleum ether (2:1 v/v), followed by ethyl acetate and then methanol/ethyl acetate (1:9 v/v), to give 5,7-diethyl-2-oxo-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)methyl]-1,2-dihydro-1,6-naphthyridin-3-carboxylic acid (A) (0.184 g) as a solid; NMR (d6 -DMSO+d4 -acetic acid): 1.15(t,3H), 1.32 (t,3H), 2.68(q,2H), 3.22(q,2H), 5.66(s,2H), 6.8-7.9(complex m,24H), 9.06(s,1H), mass spectrum (+ve FAB, DMSO/NBA): 745(M+H)+ ; microanalysis, found: C, 66.9; H, 5.0; N, 10.0%; C46H38N6O3.1.7SiO2 requires: C, 67.0; H, 4.6; N, 10.2%.

Provenance & Evidence