Hydrochloric Acid → HCID 131722219, compound

Participants

Reaction Conditions

Reaction Steps

1.19 g (2.06 mmole) of 2-[(5R)-(3,4-dichlorophenyl)-3-(3,4-dimethoxybenzenesulfonyl)oxazolidin-5-yl]ethanol t-butyldimethylsilyl ether [prepared as described in step (a) above] were dissolved in 20 ml of a 3:3:1 by volume mixture of acetic acid, tetrahydrofuran and water, and the resulting mixture was then heated at 80° C. for 2 hours under a nitrogen atmosphere. At the end of this time, the reaction mixture was then neutralised with a saturated aqueous solution of sodium hydrogencarbonate and extracted with ethyl acetate. The organic extract was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting residue was dissolved in 10 ml of pyridine. 23 mg (0.19 mmole) of 4-dimethylaminopyridine and 0.22 ml (2.84 mmole) of methanesulfonyl chloride were then added to the resulting solution, whilst ice-cooling. The mixture was then stirred for 2 hours at 0° C. under a nitrogen atmosphere. At the end of this time, the reaction mixture was poured into 200 ml of ice-cooled 10% w/v aqueous hydrochloric acid, and then extracted with ethyl acetate, The organic extract was washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting residue was purified by silica gel column chromatography, using a gradient elution method, with mixtures of hexane and ethyl acetate ranging from 2:1 to 1:2 by volume as the eluent, to give 992 mg of the title compound as white crystals.

Provenance & Evidence