4-(5-Chloro-3-methyl-benzo[b]thiophene-2-sulfonylamino)-3-methanesulfonyl-benzoic acid methyl ester → 5-chloro-N-(4-hydroxymethyl-2-methanesulfonylphenyl)-3-methylbenzo[b]thiophene-2-sulfonamide

HRID 1790223Notes

Reaction equation

HRID 1790223 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]2[S:6][C:7]([S:10]([NH:13][C:14]3[CH:23]=[CH:22][C:17]([C:18](OC)=[O:19])=[CH:16][C:15]=3[S:24]([CH3:27])(=[O:26])=[O:25])(=[O:12])=[O:11])=[C:8]([CH3:9])[C:4]=2[CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:29]=[CH:28][C:5]2[S:6][C:7]([S:10]([NH:13][C:14]3[CH:23]=[CH:22][C:17]([CH2:18][OH:19])=[CH:16][C:15]=3[S:24]([CH3:27])(=[O:26])=[O:25])(=[O:12])=[O:11])=[C:8]([CH3:9])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 101624624-(5-Chloro-3-methyl-benzo[b]thiophene-2-sulfonylamino)-3-methanesulfonyl-benzoic acid methyl esterHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 220414675-chloro-N-(4-hydroxymethyl-2-methanesulfonylphenyl)-3-methylbenzo[b]thiophene-2-sulfonamideYield 80.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
-78 °C

Procedure

Into 10 mL of toluene was dissolved 305 mg of Compound 1, and the solution was cooled to −78° C., followed by addition of 2.2 mL of 1.01 mol/L toluene solution of diisobutylaluminum hydride. After 20 minutes of stirring at the same temperature, the mixture was gradually warmed to 0° C. and stirred for 1 hour. After the reaction was terminated by adding water, the mixture was diluted with ethyl acetate and saturated aqueous potassium sodium tartrate solution were added, followed by 30 minutes of stirring at room temperature. The mixture was extracted with ethyl acetate and the organic layer was washed with saturated brine and then dried over anhydrous sodium sulfate. The solvent was removed by evaporation and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/1) to obtain 230 mg of the title compound as colorless powder.

Workup

  1. temperaturethe mixture was gradually warmed to 0° C.
  2. stirringstirred for 1 hour
  3. customAfter the reaction was terminated
  4. additionby adding water
  5. additionthe mixture was diluted with ethyl acetate and saturated aqueous potassium sodium tartrate solution
  6. additionwere added
  7. waitfollowed by 30 minutes
  8. stirringof stirring at room temperature
  9. extractionThe mixture was extracted with ethyl acetate
  10. washthe organic layer was washed with saturated brine
  11. dry with materialdried over anhydrous sodium sulfate
  12. customThe solvent was removed by evaporation
  13. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/1)

Sources & evidence

ORD record
ord-d655178a714a49b1b6bcea7037858048
Source dataset
uspto-grants-2006_07
Patent number
US07071220B2

Reaction notes

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