Acetic Acid → HCID 86691574, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (S)-ethyl 2-(4-bromo-3-methyl-1 (trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-tert-butoxyacetate (200 mg, 0.380 mmol) in dry THF (7.6 mL) was cooled to −78° C. tert-butyllithium (1.7 M in pentane, 446 μL, 0.759 mmol) was added dropwise under N2 over 3 min. 10 min later, trimethylsilylisocyanate (62.0 μL, 0.456 mmol) was quickly added. The reaction was warmed to 23° C. After 1 h, the system was treated with glacial AcOH (87.0 μL, 1.52 mmol) followed by EtOH (absolute, 1.9 mL). The reaction was stirred for 30 min then diluted with saturated NaHCO3 (20 mL) and H2O (10 mL). The system was extracted with DCM (3×15 mL). Combined organic phases were dried (Na2SO4), filtered, and concentrated. The residue was treated with benzene and wet-loaded onto a silica gel column and purified by flash chromatography (ethyl acetate/hexanes) giving the desired product (75 mg, 40% yield.) 1H NMR (400 MHz, CDCl3) δ 8.10-8.05 (m, 1H), 7.96-7.86 (m, 1H), 7.64-7.58 (m, 2H), 6.19 (s, broad, 1H), 6.06 (s, broad, 1H), 5.75 (s, 1H), 4.30-4.07 (m, 2H), 2.53 (s, 3H), 1.21 (s, 9H), 1.20 (t, J=7.0 Hz, 3H). 19F NMR (377 MHz, CDCl3) δ−73.2 (s).

Provenance & Evidence