Chlorosulfamic acid → 6-(3,5-Diisopropyl-4-sulfamoyloxy-phenyl)-hexanoic acid ethyl ester

HRID 2289681Notes

Reaction equation

HRID 2289681 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:25])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[C:16]([CH:18]([CH3:20])[CH3:19])[C:15]([OH:21])=[C:14]([CH:22]([CH3:24])[CH3:23])[CH:13]=1)[CH3:4].[S:26](Cl)(=[O:29])(=[O:28])[NH2:27]>CN(C)C=O>[CH2:3]([O:5][C:6](=[O:25])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:13]=[C:14]([CH:22]([CH3:24])[CH3:23])[C:15]([O:21][S:26](=[O:29])(=[O:28])[NH2:27])=[C:16]([CH:18]([CH3:20])[CH3:19])[CH:17]=1)[CH3:4]

Participants

5

Reactant 3

HCID 24499Chlorosulfamic acidHCID 24758Sodium hydrideHCID 539382746-(4-Hydroxy-3,5-diisopropyl-phenyl)-hexanoic acid ethyl ester

Product 1

HCID 544531636-(3,5-Diisopropyl-4-sulfamoyloxy-phenyl)-hexanoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.257 g, 6.4 mmol) was added to 6-(4-hydroxy-3,5-diisopropyl-phenyl)-hexanoic acid ethyl ester (1.46 g, 5.0 mmol) in dimethylformamide (20 mL) at 0° C. over about 3 minutes. The cooling bath was removed, and the mixture was stirred at room temperature for 10 minutes. The reaction mixture was cooled to zero degrees and sulfamoyl chloride (1.18 g, 10.3 mmol) was added over ~ 3 minutes. The reaction mixture was stirred 1.5 hours at zero degrees and was quenched by adding saturated aqueous sodium bicarbonate solution. The mixture is diluted with diethyl ether (300 mL) and water (100 mL). The organic layer is washed with water (3×100 mL), brine, dried over magnesium sulfate, filtered, and concentrated to an oil. The oil is chromatographed on silica gel using 4:1 hexanes/ethyl acetate as eluant. The title compound is obtained as a light yellow oil, 1.29 g. CI Mass Spectrum: [M+H+ ]+ =400.

Workup

  1. customThe cooling bath was removed
  2. temperatureThe reaction mixture was cooled to zero degrees
  3. stirringThe reaction mixture was stirred 1.5 hours at zero degrees
  4. customwas quenched
  5. additionby adding saturated aqueous sodium bicarbonate solution
  6. additionThe mixture is diluted with diethyl ether (300 mL) and water (100 mL)
  7. washThe organic layer is washed with water (3×100 mL), brine
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated to an oil
  11. customThe oil is chromatographed on silica gel using 4:1 hexanes/ethyl acetate as eluant

Sources & evidence

ORD record
ord-f7983db4bf30406f845bb22d9d25146e
Source dataset
uspto-grants-2000_07
Patent number
US06093744

Reaction notes

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