Methyl chloroformate → HCID 24896269, compound

Participants

Reaction Steps

To a solution of (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-(isobutylamino)-5-(trifluoromethoxy)benzyl]-4-methyl-1,3-oxazolidin-2-one (25.6 mg, 0.0502 mmol) in CH2Cl2 (0.5 mL) was added methyl chloroformate (7.7 μL, 0.100 mmol), followed by EtN(i—Pr)2 (70 μL, 0.402 mmol) The reaction was stirred at room temperature for 24 hours, and then methyl chloroformate (7.7 μL, 0.100) and EtN(i—Pr)2 (70 μL, 0.402 mmol) were added. The reaction was stirred for 96 hours and then diluted with EtOAc (20 mL), and washed with saturated NaHCO3 solution, brine, and 1 N HCl (10 mL each). The organic layer was dried over Na2SO4, filtered, and concentrated. Purification of the residue by PTLC (25% EtOAc/hexanes) afforded methyl [2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-4-(trifluoromethoxy)phenyl]isobutylcarbamate. Rf=0.29 (25% EtOAc/hexanes). LCMS=617.3 (M+1)+. 1H NMR (CDCl3, 500 MHz) δ 7.89-7.87 (m, 1H), 7.78-7.76 (m, 2H), 7.24-7.17 (m, 3H), 5.73-5.71 (m, 1H), 5.01-4.75 (m, 2H), 4.07-3.06 (m, 3H), 1.83-1.75 (m, 1H), 1.27-1.21 (m, 3H), 0.99-0.91 (m, 6H), 0.70-0.68 (m, 3H).

Provenance & Evidence