Water → HCID 21474716, compound

1.2 ml of a 1.0M solution of tetrabutyl ammonium fluoride in tetrahydrofuran were added dropwise to a solution of 152 mg of 3-(2-t-butyldimethylsilyloxy-1-methylethyl)-5-(3-chlorophenoxymethyl)oxazolidin-2-one (prepared as described in Preparation 11) in 1 ml of tetrahydrofuran, whilst ice-cooling. The mixture was then stirred at room temperature for 1.5 hours. At the end of this time, water and sodium chloride were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and then the ethyl acetate was removed from the extract by evaporation under reduced pressure. The resulting residue was purified by silica gel column chromatography, using a gradient elution method, with mixtures of ethyl acetate and ethanol in ratios ranging from 1:0 to 20:1 by volume as the eluent, to give 97 mg of the title compound having an Rf value of 0.28 (on silica gel thin layer chromatography, using ethyl acetate as the developing solvent).

1. temperaturecooling
2. extractionthe mixture was extracted with ethyl acetate
3. dry with materialThe extract was dried over anhydrous sodium sulfate
4. customthe ethyl acetate was removed from the
5. extractionextract by evaporation under reduced pressure
6. customThe resulting residue was purified by silica gel column chromatography
7. washa gradient elution method

ORD record

ord-b0e26a61a2604342a50b6c5f3f436568

Source dataset

uspto-grants-1996_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05578620