Triethylamine → Trans-2-[(tertiary-butylcarbonyloxy)methyloxycarbonyl]-5,7-dichloro-4-phenylmethylcarbonylamino-1,2,3,4-tetrahydroquinoline

Participants

Reaction Steps

To a solution of trans-2-carboxy-5,7-dichloro-4-phenylmethylcarbonylamino-1,2,3,4-tetrahydroquinoline (0.06 g, 0.16 mmol, Example 34) in tetrahydrofuran (5 ml) was added triethylamine (0.027 ml, 0.19 mmol) followed by a solution of iodomethylpivalate (0.06 g, 0.24 mmol) in tetrahydrofuran (2 ml). This mixture was stirred at room temperature for 4 hours. The solvent was removed under vacuum and the residue obtained was purified by flash chromatography (using ethyl acetate in hexane as eluent) to give the title compound (0.044 g), m.p. 162.4°-163° C. δ (360 MHz, DMSO) 1.41 (9H, s, C(CH3)3, 1.66 (1H, ddd, J=13.4, 12.6 and 3.8 Hz, CHACHBHCCHD), 2.12 (1H, dm, J=13.4 Hz, CHACHBHCCHD), 3.41 (2H, NHCOCH2Ph), 3.97 (1H, dd, J=12.6 and 3.8 Hz, CHACHBHCCHD), 5.02 (1H, m, CHACHBHCCHD), 5.81 (2H, 2d, J=5.9 Hz, CO2CH2CO), 6.71 (1H, d, J=2.0 Hz, 6-H or 8-H), 6.86 (1H, d, J=2.0 Hz, 6-H or 8-H), 6.97 (1H, bs, ArNH), 7.26 (5H, m, ArH), 8.45 (1H, d, J=7.1 Hz, CHDNHCO); m/e (CI+) 493 (M+1). Found C, 58.37; H, 5.33; N, 5.69; C24H26Cl2N2O5 requires C, 58.43; H, 5.31; N, 5.68%.

Provenance & Evidence