Reaction Steps
A mixture of 4-tert-butoxycarbonylaminomethyl-2-tert-butoxycarbonylmethoxyaniline (202 mg, 0.574 mmol), methyl 1-benzenesulfonyl-7-chloro-3-carboxymethyl-1,3,4,5-tetrahydrobenz[cd]indole-2-carboxylate (250 mg, 0.574 mmol), triethylamine (0.2 mL, 1.43 mmol), and N,N-bis(2-oxo-3-oxazolidinyl)-phosphinic chloride (Bop-Cl, 161 mg, 0.631 mmol) in dichloromethane (5 mL) was stirred for 15 h at room temperature and diluted with ethyl acetate. The mixture was washed successively with 5% potassium hydrogen sulfate, water, saturated sodium bicarbonate, water, and brine, dried over magnesium sulfate, and concentrated to give 463 mg of the title compound (quant): 1H NMR (CDCl3) δ8.63 (s, 1H), 8.33 (d, 1H, J=8.6 Hz), 8.03 (d, 2H, J=6.9 Hz), 7.92 (s, 1H), 7.58 (t, 1H, J=6.9 Hz); 7.52 (t, 2H, J=6.9 Hz), 7.06 (s, 1H), 6.94 (d, 1H, J=Hz), 6.80 (s, 1H), 4.82 (br, 1H), 4.35 (s, 2H), 4.12 (d, 2H, J=7.3 Hz), 3.89 (s, 3H), 3.86 (m, 1H), 3.03 (mt, 1H, J=14.7 Hz), 2.81 (m, 1H), 2.81 (dd, 1H, J=14.7, 4.3 Hz), 2.53 (dd, 1H, J=14.7, 10.4 Hz), 2.22 (m, 1H), 1.72 (m, 1H), 1.46 (s, 9H), 1.45 (s, 9H).
