Acetyl chloride → HCID 59485887, compound

Participants

Reaction Steps

To a solution of (S)-2-[3-[4-(4-chloro-phenoxy)-phenyl]-2-oxo-4-(3-trifluoromethyl-phenyl)-imidazolidin-1-yl]ethanesulfonic acid amide (20 mg, 0.037 mmol) and acetyl chloride (6 mg, 0.076 mmol) in anhydrous CH2Cl2 (1 mL) is added triethylamine (7.7 mg, 0.076 mmol). The mixture is stirred at room temperature for 14 h and is then concentrated to dryness. The residue is dissolved in EtOH and treated with NaOH (0.074 mmol, 1 M aqueous solution) for 1 h. The mixture is then treated with water (3 mL) and extracted with EtOAc (3×3 mL). The combined organic layers are concentrated and purified by flash column chromatography to provide the title compound as a white solid. 1H NMR (CDCl3, 400 MHz) δ 7.56 (m, 3H), 7.48 (m, 1H), 7.24 (d, J=8.8 Hz, 2H), 7.20 (d, J=8.8 Hz, 2H), 6.86 (d, J=9.2 Hz, 2H), 6.85 (d, J=8.8 Hz, 2H), 5.26 (dd, J=9.2, 6.8 Hz, 1H), 4.00 (t, J=9.2 Hz, 1H), 3.75-3.90 (m, 2H), 3.55-3.65 (m, 2H), 3.36 (dd, J=8.8, 6.8 Hz, 1H), 2.17 (s, 3H); HPLC-MS calculated for C26H23ClF3N3O5S (M+H+) 582.1, found 582.1.

Provenance & Evidence