Trifluoroacetic acid → HCID 178517351, compound

Participants

Reaction Steps

To a solution of racemic (1S,2R) and (1R,2S)-2-(4-chlorophenyl)-1′-(1-trityl-1H-imidazol-4-yl)spiro[cyclopropane-1,3′-indolin]-2′-one (115 mg, 0.2 mmol) in DCM (2 mL) and water (0.5 mL) was added TFA (0.1 mL) dropwise at 0° C. The mixture was stirred for 14 hours at room temperature. The mixture was poured into the sat. aqueous NaHCO3 solution, extracted with DCM (3×10 mL), dried and concentrated to give the title product. The residue was dissolved in 2 mL of DMF. Purification by preparative HPLC gave the title compound as white powder (60 mg, 89%). LC/MS m/e calcd. for C19H14ClN3O: 335, observed (M+H)+: 336.1 1H NMR (400 MHz, DMSO-d6) δppm 2.13 (dd, J=9.09, 5.05 Hz, 1 H) 2.42 (dd, J=8.08, 4.80 Hz, 1 H) 3.23 (t, J=8.72 Hz, 1 H) 6.20 (d, J=7.58 Hz, 1 H) 6.81 (t, J=7.20 Hz, 1 H) 7.16 (t, J=7.83 Hz, 1 H) 7.30-7.45 (m, 5 H) 7.66 (s, 1 H) 8.27 (s, 1 H). MS calcd. for C19H14ClN3O 335, obsd. (ESI+) [(M+H)+] 336.3.

Provenance & Evidence