m-Chloroperbenzoic acid → HCID 25010057, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 4′-methoxy-2-methyl-2″-{[(4S,5R)-4-methyl-2-oxo-5-pyridin-4-yl-1,3-oxazolidin-3-yl]methyl}-4″-(trifluoromethyl)-1,1′:3′,1″-terphenyl-4-carboxylate (175 mg, 0.296 mmol) in CH2Cl2 (15 mL) at 0° C. under N2, was added 3-chloroperbenzoic acid (146 mg, 0.593 mmol) as a powder. The mixture was stirred at 0° C. for 15 min. Then it was allowed to warm up to room temperature and stirred for 2 h. The reaction mixture was diluted with CH2Cl2 and washed with satd Na2SO3 (1×) followed satd K2CO3 (2×). The organic layer was dried (Na2SO4), filtered and the solvent was evaporated in vacuo. The residue obtained was dissolved in POCl3 (10 mL). The resulting solution was heated at 110° C. under N2 for 2 h. Then it was allowed to warm to room temperature and stirred for 2 h. The reaction was concentrated in vacuo. The residue was diluted with EtOAc (50 mL) and water (10 mL) and washed with satd NaHCO3 (20 mL). The aqueous layer was extracted with EtOAc (2×40 mL). The combined organic layers were dried (Na2SO4), filtered and the solvent was evaporated in vacuo. The residue was purified by flash chromatography on silica gel to give methyl 2″-{[(4S,5R)-5-(2-chloropyridin-4-yl)-4-methyl-2-oxo-1,3-oxazolidin-3-yl]methyl}-4′-methoxy-2-methyl-4″-(trifluoromethyl)-1,1′:3′,1″-terphenyl-4-carboxylate. LCMS calc.=625.2; found=625.0 (M+1)−. 1H NMR (500 MHz, CDCl3, 1:1 mixture of atropisomers) δ 8.40 (s, 0.5 H); 8.39 (s, 0.5 H); 7.97 (s, 1 H); 7.90 (t, J=5.8 Hz, 1 H); 7.72 (s, 0.5 H); 7.69-7.63 (m, 1.5 H); 7.48 (d, J=11.8 Hz, 0.5 H); 7.44 (s, 0.5 H); 7.43-7.37 (m, 1 H); 7.32-7.26 (m, 1 H); 7.24 (s, 0.5 H); 7.20 (s, 0.5 H); 7.16 (d, J=2.2 Hz, 0.5 H); 7.14 (d, J=2.2 Hz, 0.5 H); 7.12-7.06 (m, 1.5 H); 7.05 (d, J=5.1 Hz, 0.5H); 5.42 (d, J=8.1 Hz, 0.5H); 5.18 (d, J=8.1 Hz, 0.5 H); 4.92 (dd, J=15.9, 18.5 Hz, 1 H); 4.19 (d, J=15.8 Hz, 0.5 H); 3.99 (d, J=15.8 Hz, 0.5 H); 3.95 (s, 3 H); 3.88 (s, 3 H); 3.81-3.75 (m, 1 H); 2.39 (s, 1.5 H); 2.35 (s, 1.5 H); 0.60 (d, J=6.5 Hz, 1.5 H); 0.49 (d, J=6.5 Hz, 1.5 H).

Provenance & Evidence