Lawesson's reagent → (R)-tert-Butyl 2,2,4-trimethyl-4-(5-(4-(octyloxy)-3-(trifluoromethyl)phenyl)-1,3,4-thiadiazol-2-yl)oxazolidine-3-carboxylate

Participants

Reaction Steps

A solution of (S)-tert-butyl 2,2,4-trimethyl-4-(2-(4-(octyloxy)-3-(trifluoromethyl)-benzoyl)hydrazinecarbonyl)oxazolidine-3-carboxylate (13a) (228 mg, 0.39 mmol) in toluene (5 mL) was treated with Lawesson's reagent (473 mg, 1.17 mmol) at 85° C. for 2 hours. The reaction was cooled down to room temperature and the supernatant was chromatographed on a silica gel column eluted with ethyl acetate-hexane (0-30%, v/v) to afford the title compound (156 mg, 70% yield). MS (ESI): 572.17 (MH+), 1H NMR (400 MHz, CDCl3) δ 8.10 (d, 1H, J=8.8 Hz), 8.08 (d, 1H, J=6.8 Hz), 7.06 (d, 1H, J=8.0 Hz), 4.41 (d, 1H, J=8.0 Hz), 4.18 (d, 1H, J=9.6 Hz), 4.13-4.07 (m, 3H), 2.00 (s, 3H), 1.85 (m, 2H), 1.78 (s, 3H), 1.68 (m, 4H), 1.51 (s, 3H), 1.47 (m, 2H), 1.39-1.28 (m, 13H), 0.89 (t, 3H, J=7.2 Hz).

Provenance & Evidence