Compound 4d

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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) was added NaSMe (0.3 mmol, 21.0 mg). The reaction mixture was stirred for 4 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 4d (14.5 mg, 73% 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 9.452 min (minor) and 10.041 min (major). ¹H NMR (600 MHz, CDCl₃): δ 10.65 (s, 1H), 7.56 (t, J = 7.8 Hz, 1H), 7.50 (d, J = 7.7 Hz, 1H), 7.37 (d, J = 7.9 Hz, 1H), 6.27 (dq, J = 48.5, 6.2 Hz, 1H), 2.53 (s, 3H), 1.64 (dd, J = 24.1, 6.2 Hz, 3H). ¹³C NMR (150 MHz, CDCl₃): δ 191.26 (d, J = 4.3 Hz), 145.62 (d, J = 19.3 Hz), 144.23, 133.68 (d, J = 1.2 Hz), 129.54 (d, J = 3.6 Hz), 126.77 (d, J = 1.3 Hz), 122.29 (d, J = 14.1 Hz), 88.28 (d, J = 167.9 Hz), 23.76 (d, J = 25.1 Hz), 17.06.