Aniline → HCID 86747052, compound

Participants

Reaction Steps

Trans-4-carboxymethyl-2-tertiarybutyloxycarbonyl-5,7-dichloro-1,2,3,4-tetrahydroquinoline (0.25 g, 0.000696M) was dissolved in dry THF with dry triethylamine (0.29 ml, 3 molar equivalents), hydroxybenzotriazole (0.141 g, 1.5 molar equivalents), aniline (0.0925 ml, 1.5 molar equivalents) and 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (0.2 g, 1.5 molar equivalents) and the reaction mixture was stirred at room temperature for 14 h. The solvents were removed in vacuo and the residue was dissolved in ethyl acetate (100 ml) and washed successively with 0.5 normal citric acid solution (3×50 ml), saturated sodium hydrogen carbonate solution (3×50 ml) and brine (1×50 ml), dried (Na2SO4), filtered and evaporated under vacuum. The residue obtained was purified by chromatography on silica gel using 10% ethyl acetate in hexane as eluent to give the title compound (0.14 g) as a colourless oil; δ (250 MHz, DMSO) 1.48 (9H, s, (CH3)3C), 1.69 (1H, ddd, J=13.0, 12.4 and 4.0 Hz, CHACHBHCCHD), 2.47 (2H, m, CHACHBHCCHDCHEHFCONHPh), 2.73 (1H, dd, J=16.5 and 2.5 Hz, CHACHBHCCHDCHEHFCONHPh), 3.73 (1H, m, CHACHBHCCHDCHEHFCONHPh), 3.98 (1H, dd, J=12.4 and 3.3 Hz, CHACHBHCCHDCHEHFCONHPh), 4.72 (1H, br, s, ArNHCHA), 6.50 (1H, d, J=2.0 Hz, 6-H or 8-H), 6.70 (1H, d, J=2.0 Hz, 6-H or 8-H), 7.15 (2H, m, p-proton and PhNH), 7.33 (2H, t, J=7.5 Hz, m protons), 7.50 (2H, d, J=7.5 Hz, o protons); m/e (FAB) 379 (M+1).

Provenance & Evidence