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

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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) (0.0105 g, 0.025 mmol) and Et3N (0.017 ml, 0.123 mmol) in CH2Cl2 (2 mL) was added benzoyl chloride (8.53 μl, 0.074 mmol) at room temperature. After 3 h, the reaction mixture concentrated and purified by preparative-HPLC (MeCN/H2O/NH4OAc) to afford 2-(6-benzoyl-4-(4-fluorophenyl)-2-isopropyl-8,8-dimethyl-5,6,7,8-tetrahydro-1,6-naphthyridin-3-yl)-2-tert-butoxyacetic acid (0.0102 g, 77% yield) as a white powder. 1H NMR (500 MHz, CD3OD) δ ppm 6.94-7.58 (9H, m), 4.79 (1H, br. s.), 4.59 (0.5H, d, J=17.4 Hz), 4.40 (0.5H, d, J=17.7 Hz), 4.30 (0.5H, d, J=16.5Hz), 4.00 (0.5H, d, J=12.5 Hz), 3.92 (0.5H, d, J=16.5Hz), 3.77 (0.5H, d, J=12.8 Hz), 3.54-3.64 (2H, m), 1.43 (3H, d, J=19.2 Hz), 1.12-1.35 (9H, m), 0.98 (4H, br. s.), 0.94 (5H, br. s.). LCMS (M+H) calcd for C32H38FN2O4: 533.28. found: 533.4.

Provenance & Evidence