Water → Benzenesulfonamide

To a solution of 4-chloro-N-[5-chloro-2-chlorophenyl]benzenesulfonamide (1.00 g, 2.97 mmol), triphenylphosphine (1.64 g, 6.24 mmol) and 5S-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-pentanol (1.30 g, 5.94 mmol) in THF (12 mL) was added diisopropylazodicarboxylate (1.23 mL, 6.24 mol) dropwise at 0° C. under nitrogen. The resulting mixture was allowed to warm to 22 DC with stirring. Stirring was continued for a period of 12 h followed by the addition of 25 mL of H2O. The mixture was extracted with ether (3×25 mL). The combined organic extracts were washed with 1M NaHCO3 and sat. brine. The organic phase was dried over Na2SO4, filtered, and concentrated under reduced pressure. Silica gel chromatography (1:5 ethyl acetate:hexanes) of the concentrate afforded 830 mg of 4-chloro-N-[5-chloro-2-chlorophenyl]-N-[(R)-1-methyl-4-[(1,1-dimethylethyl)-dimethylsilyl]oxy)butyl]benzenesulfonamide as a yellow oil in 52% yield.

1. temperatureto warm to 22 DC
2. stirringStirring
3. extractionThe mixture was extracted with ether (3×25 mL)
4. washThe combined organic extracts were washed with 1M NaHCO3 and sat. brine
5. dry with materialThe organic phase was dried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure

ORD record

ord-4eb9234eafc340dda5e645cf6e47ab14

Source dataset

uspto-grants-2005_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06967196B1