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(5R)-3-(4-(1,2,5,6-Tetrahydropyridin-4-yl)-3-fluorophenyl)-5-(1,2,3-triazol-1-ylmethyl)-oxazolidin-2-one hydrochloride (380 mg, 1 mM) was dissolved in water (5 ml), which was then diluted with acetone (10 ml), and solid sodium bicarbonate (0.84 g, 10 mM) added. The mixture was stirred and cooled to 0° C., and isopropylsulfonyl chloride (285 mg, 2 mM) added dropwise. After stirring for 5 hours, an equal portion of sulfonyl chloride was added, and stirring continued for 18 hours. Most acetone was removed by evaporation, the residue diluted with water (50 ml), and extracted with ethyl acetate (3×20 ml). The extracts were washed with brine and dried (magnesium sulfate). The residual oil after evaporation was purified by chromatography on a 10 g silica Mega Bond Elut® column, eluting with a gradient increasing in polarity from 0 to 5% methanol in dichloromethane. Relevant fractions were combined and evaporated to give the desired product (205 mg).

1. additionadded
2. stirringAfter stirring for 5 hours
3. stirringstirring
4. customMost acetone was removed by evaporation
5. additionthe residue diluted with water (50 ml)
6. extractionextracted with ethyl acetate (3×20 ml)
7. washThe extracts were washed with brine
8. dry with materialdried (magnesium sulfate)
9. customThe residual oil after evaporation
10. customwas purified by chromatography on a 10 g silica Mega Bond Elut® column
11. washeluting with
12. temperaturea gradient increasing in polarity from 0 to 5% methanol in dichloromethane
13. customevaporated