Triethylamine → 2-Tert-butoxy-2-[6-(4-fluorobenzoyl)-4-(4-fluorophenyl)-2-isopropyl-8,8-dimethyl-5,7-dihydro-1,6-naphthyridin-3-yl]acetic acid

Participants

Reaction Steps

To a stirred turbid mixture of 2-tert-butoxy-2-(4-(4-fluorophenyl)-2-isopropyl-8,8-dimethyl-5,6,7,8-tetrahydro-1,6-naphthyridin-3-yl)acetic acid (example 1) (0.0103 g, 0.024 mmol) and Et3N (0.017 ml, 0.120 mmol) in CH2Cl2 (2 mL) was added 4-fluorobenzoyl chloride (8.52 μl, 0.072 mmol) at room temperature. After 3 h, the reaction mixture concentrated and purified by preparative-HPLC (MeCN/H2O/NH4OAc) to afford 2-tert-butoxy-2-(6-(4-fluorobenzoyl)-4-(4-fluorophenyl)-2-isopropyl-8,8-dimethyl-5,6,7,8-tetrahydro-1,6-naphthyridin-3-yl)acetic acid (0.0104 g, 77% yield) as white powder. 1H NMR (500 MHz, CD3OD) δ ppm 6.98-7.59 (8H, m), 4.75-4.87 (1H, br. s.), 4.57 (0.5H, d, J=17.7 Hz), 4.40 (0.5H, d, J=17.7 Hz), 4.31 (0.5H, d, J=17.7 Hz), 4.02 (0.5H, d, J=11.6 Hz), 3.92 (0.5H, d, J=15.3 Hz), 3.73 (0.5H, d, J=12.5Hz), 3.53-3.78 (2H, m), 1.37-1.48 (3H, m), 1.19-1.35 (6H, m), 1.15 (3H, d, J=6.1 Hz), 0.96 (9H, br. s.). LCMS (M+H) calcd for C32H37FN2O4: 551.27. found: 551.4.

Provenance & Evidence