Compound 4e

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Compound data: HPLC

Compound data: 1H NMR

Compound data: 13C NMR

Compound data: 19F NMR

Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.

To a solution of 3k (0.1 mmol, 17.0 mg) in DMF (0.5 mL) were added ethyl thioglycolate (0.3 mmol, 33 uL) and K₂CO₃ (0.3 mmol, 41.5 mg). The reaction mixture was stirred for 3 h at 60 ^oC. Upon completion, the reaction mixture was diluted with ethyl acetate and washed with water and brine. The combined organic layers were dried over Na₂SO₄, filtered and concentrated in vacuo. The crude residue was purified by preparative TLC to afford 4e (21.6 mg, 86% yield, 96% ee). The ee value was determined by SFC analysis on a Chiralcel OD-3 column (0% isopropanol, 2.0 mL/min) with retention time of 16.736 min (minor) and 22.323 min (major). ¹H NMR (600 MHz, CDCl₃): δ 8.22 (s, 1H), 7.83 (d, J = 8.1 Hz, 1H), 7.46 (t, J = 7.7 Hz, 1H), 7.41 (d, J = 7.3 Hz, 1H), 6.06 (dq, J = 46.9, 6.5 Hz, 1H), 4.42 (q, J = 7.1 Hz, 2H), 1.78 (dd, J = 23.7, 6.5 Hz, 3H), 1.43 (t, J = 7.1 Hz, 3H). ¹³C NMR (150 MHz, CDCl₃): δ 162.70, 143.06, 137.98 (d, J = 19.6 Hz), 135.41 (d, J = 3.4 Hz), 134.40, 127.92 (d, J = 2.2 Hz), 126.75, 122.77 (d, J = 1.7 Hz), 121.21 (d, J = 8.2 Hz), 89.77 (d, J = 169.0 Hz), 61.73, 22.63 (d, J = 25.2 Hz), 14.35. ¹⁹F NMR (376 MHz, CDCl₃): δ –169.23. HRMS (ESI-TOF): m/z calculated for C₁₃H₁₄FO₂S⁺ [M+H]⁺ 253.0693, found 253.0693.