Sodium Carbonate → HCID 68849304, compound

Participants

Reaction Conditions

Reaction Steps

43 ml (272 mmol) of triethylsilane are added dropwise to a solution of 17 ml (136 mmol) of boron trifluoroetherate in 150 ml of dichloromethane cooled beforehand to 0° C. After stirring for 15 minutes, 10 g (17 mmol) of tert-butyl N-{4′-[3-(4-benzyl-2-oxooxazolidin-3-yl)-2-ethoxy-1-hydroxy-3-oxopropyl]biphenyl-3-ylmethyl}-N-methylcarbamate dissolved in 70 ml of dichloromethane are added dropwise. The reaction medium is stirred from 0° C. to room temperature for 3 hours and then heated at 40° C. for 48 hours, treated with saturated aqueous sodium carbonate solution, extracted with dichloromethane, dried over magnesium sulfate, filtered and concentrated. The residue obtained is purified by chromatography on a column of silica eluted with a dichloromethane/methanol/triethylamine mixture (95/5/0.5). 8 g of 4-benzyl-3-[2-ethoxy-3-(3′-methylaminomethylbiphenyl-4-yl)propionyl]oxazolidin-2-one are obtained in a yield of 13% to 3 g of methyl 2-ethoxy-3-hydroxy-3-(3′-methylaminomethylbiphenyl-4-yl)propionate are obtained in a yield of 51%.

Provenance & Evidence