Tributylphosphine → HCID 54491673, compound

Participants

Reaction Steps

A cooled (0° C.) solution of (1R,2R)-2-(4-cyanophenyl)-N-[2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-N-(2-hydroxyethyl)-4-methylthiazole-5-carboxamide (0.45 g, 0.83 mmol, obtained in example 82) in THF (10 mL) was treated with diethylazadicarboxylate (0.20 mL, 1.25 mmol) and tributylphosphine (0.31 mL, 1.25 mmol) for 20 h at room temperature. The mixture was evaporated to dryness and the residue was purified by flash chromatography to give the title compound as a white solid: mp 150°-160° C.; 1H NMR (300 MHz, CDCl3) δ (TMS) 8.06 (d, J=8.4, 2H, arom), 7.76 (s, 1H, triazole), 7.76 (d, J=8.4, 2H, arom), 7.30 (s, 1H, triazole), 7.4-7.2 (m, 1H, arom), 7-6.7 (m, 2H, arom), 5.53 (br), 5.17 (d, J=15.1, 1H, TrCH(H)), 4.7 (br d, 1H), 4.6-4.4 (m, 1H), 4.0 (br d), 3.6 (br s), 2.57 (s, 3H, Me-thiazole), 1.13 (d, J=6.8, 3H, MECH); GC--MS 293 (M+ -acyl, C14H15N4F2O), 227 (acyl group, C12H7N2OS); [α]D =-80.5° (c 1, CHCl3).

Provenance & Evidence