Triethylamine → HCID 67334794, compound

Participants

Reaction Steps

To a solution of the intermediate from step F (100 mg, 0.225 mmol) in DCM (3 mL) was added triethyl amine (94 μl, 0.675 mmol) followed by trimethyl acetyl chloride (33.25 μL, 0.27 mmol). After 2 hours the reaction was diluted with DCM (10 mL) and washed with 1N HCl, saturated Na2CO3, dried over brine and concentrated in vacuo to give a colorless oil. This material was dissolved in THF (2 mL) and MeOH (1 mL) and 2N NaOH (2 mL) were added and the reaction left stirring at room temperature for 16 hours. The reaction was concentrated in vacuo. The residue was suspended in 1N HCl (until the pH was less then 2). The resulting suspension was extracted with EtOAc (3×), dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give the title compound as a white solid. 1H NMR (DMSO, 500 MHz): δ 7.93 (d, J=8.2 Hz, 2H), 7.81 (d, J=1.8 Hz, 2H), 7.51 (t, J=2.1 Hz, 1H), 7.26 (d, J=8.3 Hz, 2H), 6.94 (s, 1H), 5.54 (s, 2H), 4.34 (d, J=13.3 Hz, 2H), 3.0 (m, 1H), 2.86 (t, J=12.9 Hz, 2H), 2.51 (t, J=1.6 Hz, 1H), 1.74 (d, J=11 Hz, 2H), 1.44 (dq, J=3.4, 12.8 Hz, 2H), 1.2 (s, 9H).

Provenance & Evidence