Sodium Thiosulfate → HCID 12112439, compound

Participants

Reaction Steps

To a solution of N-[5-fluoro-2-(2,2,2-trifluoro-1-hydroxyethyl)phenyl]benzenepropanamide from Step 4 (178 mg, 0.521 mmol) and methylene chloride (15 mL) was added 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxyl-3(1H)-one (885 mg, 2.08 mmol) followed by tert-butanol (15 mL) under an argon atmosphere at 23° C. After 18 h, sat'd NaHCO3 (31 mL) was added followed by solid sodium thiosulfate (5.20 g, 32.9 mmol). After 1 h at 23° C., the organic layer was separated from the aqueous. The aqueous was extracted with ether (2×100 mL), and the combined organics were washed with sat'd NaHCO3:sat'd Na2S2O3 (3×80 mL), brine (1×80 mL), and dried (MgSO4). After concentration in vacuo, the crude residue was purified by flash chromatography (ethyl acetate:hexane 1:3) which afforded N-[5-fluoro-2-(2,2,2-trifluoro-1-oxoethyl)phenyl]benzenepropanamide (80 mg) as a yellow gum: 1H NMR (CDCl3) δ2.78 (t, J=7 Hz), 3.07 (t, J=7 Hz), 6.82-6.91 (m), 7.17-7.33 (m), 7.92-8.03 (m), 8.67-8.73 (m), 11.11 (br s); 13C NMR (CDCl3) δ31.0, 40.2, 108.2 (d, J=27.8 Hz), 110.45 (d, J=22.5 Hz), 111.6, 116.4 (q, J=290 Hz), 126.4, 128.2, 128.5, 134.5 (d, J=5 Hz), 139.9, 139.9, 146.2 (d, J=14 Hz), 167.9 (d, J=258 Hz), 171.6,181.9. MS (EI) 339 (M+), 320, 270, 207. IR (neat) 1712, 1677 cm−1. Anal. Calc'd. for C17H13NO2F4: C, 60.18; H, 3.86; N, 4.13. Found: C, 59.82; H, 4.08; N, 3.94.

Provenance & Evidence