Lithium hydroxide, monohydrate → 4-[2-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulen-8-yl]-5,6-dihydro-2H-pyridine-1,3-dicarboxylic acid 1-tert-butyl ester

Participants

Reaction Steps

4-[2-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulen-8-yl]5,6-dihydro-2H-pyridine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester (0.629 g, 1.18 mmol) and lithium hydroxide monohydrate (4.8 mmol) in THF (4 mL) and water (2 mL) were heated at 60° C. overnight. The reaction mixture was cooled to RT, THF removed in vacuo and the residue acidified to pH 3 with 1M HCl. The resultant solid was filtered off, washed with water and dried. The resultant solid was subjected to flash chromatography (SiO2, gradient 0 to 10% methanol in DCM) to give 4-[2-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulen-8-yl]-5,6-dihydro-2H-pyridine-1,3-dicarboxylic acid 1-tert-butyl ester (0.31 g, 51%). 1H NMR 300 MHz (CDCl3) δ: 8.27 (1 H, d, J=8.34 Hz), 7.93 (1 H, s), 7.17 (1 H, s), 7.07 (1H, dd, J=8.31, 1.80 Hz), 6.55 (1 H, s), 6.10 (1 H, m), 4.40 (2 H, m), 4.14 (4 H, m), 3.67 (2 H, m), 2.50 (2H, m), 1.63 (6 H, d, J=6.58 Hz), 1.54 (9 H, s).

Provenance & Evidence