Triethylamine → HCID 86707792, compound

Participants

Reaction Steps

To a stirred solution of triethyl amine trihydrofluoride (4.21 g, 26.16 mmol, 4 eq.) in DCM (25 mL) was added triethyl amine (1.32 g, 13.08 mmol) in drop wise manner at −78° C. After 15 minutes was added X-TalFluoro-M (4.74 g, 19.62 mmol) followed by addition of pre-dissolved solution of 3-hydroxy-3-{4-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-phenyl}-cyclobutanecarboxylic acid ethyl ester (Preparation 3, 3.5 g, 6.54 mmol) in DCM (15 mL) at −78° C. Resulting reaction mixture was stirred at room temperature for 16 hours. After consumption of starting material, reaction mixture was quenched with saturated aqueous solution of sodium bicarbonate (50 mL) and stirred at room temperature for 0.5 hours. Aqueous layer was extracted with DCM (3×50 mL). Combined organic layers were dried over sodium sulphate, filtered and evaporated. Purification was done by column chromatography on silica gel (100-200 mesh size). Compounds were eluted using 5% ethyl acetate in hexane to afford two off-white solids (2 g-non-polar spot, and 1.2 g-polar spot). 1H NMR (400 MHz, CDCl3) (Non Polar spot) δ: 1.26 (t, J=7.12 Hz, 3H), 2.80 (d, J=8.76 Hz, 2H), 2.87 (d, J=8.72 Hz, 2H), 3.47-3.49 (m, 1H), 3.67 (d, J=17.16 Hz, 1H), 4.08 (d, J=17.16 Hz, 1H), 4.16 (q, J=7.2 Hz, 2H), 7.51 (d, J=8.12 Hz, 2H), 7.63 (s, 2H), 7.67 (d, J=8.16 Hz, 2H); LC-MS (m/z): 536.00 (M−H).

Provenance & Evidence