Reaction Steps
A mixture of potassium losartan (974 mg, 2.11 mmol), (1R,3S,4S)-3-methoxy-4-(nitrooxy)cyclopentanecarboxylic acid (intermediate 1, 429 mg, 2.09 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (447 mg, 2.33 mmol), and N-methylmorpholine (0.50 mL, 4.6 mmol) was dissolved in dichloromethane (20 mL) and stirred for 2 days with catalytic amounts of 4-(dimethylamino)pyridine. 1H NMR (500 MHz, CDCl3) δ 0.84 (t, J=7.3 Hz, 3H), 1.28 (sextet, J=7.3 Hz, 2H), 1.56 (quintet, J=7.3 Hz, 2H), 1.78-1.84 (m, 1H), 1.88-1.92 (m, 1H), 2.08-2.15 (m, 1H), 2.30-2.36 (m, 1H), 2.38 (t, J=6.7 Hz, 2H), 2.71 (quintet, J=8.2 Hz, 1H), 3.26 (s, 3H), 3.70-3.75 (m, 1H), 4.87 (d, J=13.9 Hz, 1H), 4.91 (d, J=13.7 Hz, 1H), 5.13 (s, 2H), 5.15-5.19 (m, 1H), 6.77 (d, J=8.0 Hz, 2H), 7.10 (d, J=8.2 Hz, 2H), 7.41 (d, J=7.8 Hz, 1H), 7.52 (td, J=1.4, 7.6 Hz, 1H), 7.61 (td, J=1.4, 7.6 Hz, 1H), 7.84 (dd, J=0.9, 7.7 Hz, 1H); LC-MS: m/z 610.4 (M+H).
