HCID 86747052, compound → HCID 44301977, compound

Participants

Reaction Steps

Trans-4-phenylaminocarbonylmethyl-2-tertiarybutyloxycarbonyl-5,7-dichloro-1,2,3,4-tetrahydroquinoline (0.12 g) was dissolved in 10% aqueous trifluoroacetic acid (30 ml) and stood at room temperature for 30 mins. The solvents were removed under vacuum and the residue chromatographed on silica gel using 3% methanol, 1% acetic acid, 96% dichloromethane to give a solid which was recrystallised from diethyl ether/hexane to give the title compound as a colourless solid (0.035 g, m.p. 208° C. dec); δ (360 MHz, DMSO) 1.62 (1H, ddd, J=13.0, 12.4 and 3.9 Hz, CHACHBHCCHD), 2.19 (1H, d, J=13.0 Hz, CHACHBHCCHD), 2.49 (2H, m, CHEHFCONHPh), 3.58 (1H, m, CHACHBHCCHD), 4.08 (1H, dd, J=12.4 and 3.4 Hz, CHACHBHCCHD), 6.62 (2H, m, 6-H or 8-H and NH), 6.80 (1H, d, J=2.0 Hz, 6-H or 8-H), 7.04 (1H, t, J=7.4 Hz, p proton), 7.31 (2H, t, J=7.4 Hz, m protons), 7.59 (2H, d, J=7.4 Hz, o protons); m/e (FAB) 379 (M+1); Found C, 57.18; H, 4.31; N, 7.22. C18H16Cl2N2O3 requires C, 57.01; H, 4.25; N, 7.39%.

Provenance & Evidence