Triphenylphosphine → Benzenesulfonamide
Reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11]C2C=C(Cl)C=CC=2COOC(=O)C)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC([Si](C)(C)OCC(O)CCC)(C)C.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1.O>[C:5]1([S:8]([NH2:11])(=[O:10])=[O:9])[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1Participants
Conditions
- Temperature
- 22 °C
Procedure
To a solution of 4-chloro-N-[5-chloro-2-(acetoxyoxymethyl)phenyl]benzenesulfonamide (13.7 g, 36.6 mmol), triphenylphosphine (21.1 g, 80.6 mmol) and 5S-[[(1,1-dimethylethyl)dimethylsilyl]oxy-2-pentanol (16.0 g, 73.3 mmol) in THF (130 mL) was added diisopropylazodicarboxylate (15.9 mL, 80.6 mmol) dropwise at 0° C. under nitrogen. The resulting mixture was allowed to warm to 22° C. with stirring. Stirring was continued for a period of 12 h followed by the addition of 150 ml of H2O. The mixture was extracted with ether (3×100 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 16.6 g of 4-chloro-N-[5-chloro-2-(acetoxymethyl)phenyl]-N-[(R)-1-methyl-4-[(1,1-dimethylethyl)dimethylsilyl]oxy)butyl]benzenesulfonamide as a yellow oil in 79% yield.
Workup
- stirringStirring
- extractionThe mixture was extracted with ether (3×100 mL)
- washThe combined organic extracts were washed with 1M NaHCO3 and sat. brine
- dry with materialThe organic phase was dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-7f8d880efcc642e59d13a177d0bebcf4
- Source dataset
- uspto-grants-2005_11
- Patent number
- US06967196B1
Reaction notes
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