Reaction Steps
To a solution of trans-4(4-tertiary-butyloxycarbonylaminoethylphenyl)methylcarbonylamino-5,7-dichloro-2-methoxycarbonyl-1,2,3,4-tetrahydroquinoline (Example 106c) (0.150 g, 0.28 mmol) in ethyl acetate (5 ml) was added a saturated solution of hydrogen chloride in ethyl acetate (5 ml) and the resulting mixture was stirred at room temperature for 40 minutes. The solvent was then removed under vacuum and the residue was triturated with hot ethyl acetate. A gummy solid was collected by filtration and this was dissolved in water and freeze dried to give the title compound as a colourless solid (0.121 g), m.p. decomposes above 200° C. δ (360 MHz, DMSO 1.65 (1H, ddd, J=13.0, 12.5 and 3.8 Hz, CHACHBHCCHD), 2.14 (1H, dm, J=13.0 Hz, CHACHBHCCHD), 2.86 (2H, m, ArCH2CH2NH3), 3.00 (2H, m, ArCH2CH2NH3), 3.36 (2H, s, NHCOCH2Ar), 3.72 (3H, s, CO2CH3), 3.97 (1H, dd, J=12.5 and 2.5 Hz, CHACHBHCCHD), 5.00 (1H, m, CHACHBHCCHDNHCO), 6.69 (1H, d, J=2.0 Hz, 6-H or 8-H), 6.88 (1H, d, J=2.0 Hz, 6-H or 8-H), 6.93 (1H, s, ArNH), 7.17 (2H, d, J=8.2 Hz, ArH), 7.21 (2H, d, J=8.2 Hz, ArH), 8.04 (3H, brs, NH3), 8.49 (1H, d, J=7.0 Hz, CHDNHCO); m/e 435 (M+), 198 (100%, M-NHCOCH2C6H4CH2CH2NH2, CO2CH3 and H); Found C, 51.47; H, 5.37; N, 8.60; C21H23Cl2N3O3.HCl.H2O requires C, 51.39; H, 5.34; N, 8.56%.
