Potassium Carbonate → HCID 58937082, compound

HRID 855989Notes

Reaction equation

HRID 855989 reaction equation
[CH3:1][O:2][C:3](=[O:31])[C:4]1[CH:9]=[C:8]([S:10](=[O:29])(=[O:28])[N:11]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=3)=[CH:17][CH:16]=2)[CH2:12][CH2:13][CH3:14])[CH:7]=[CH:6][C:5]=1[CH3:30].I[CH2:33][CH2:34][CH3:35].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:31])[C:4]1[CH:9]=[C:8]([S:10](=[O:29])(=[O:28])[N:11]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:22]=[CH:23][C:24]([O:27][CH2:33][CH2:34][CH3:35])=[CH:25][CH:26]=3)=[CH:17][CH:16]=2)[CH2:12][CH2:13][CH3:14])[CH:7]=[CH:6][C:5]=1[CH3:30].[CH3:1][O:2][C:3](=[O:31])[C:4]1[CH:9]=[C:8]([S:10](=[O:29])(=[O:28])[N:11]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:22]=[CH:23][C:24]([OH:27])=[CH:25][CH:26]=3)=[CH:17][CH:16]=2)[CH2:12][CH2:13][CH3:14])[CH:7]=[CH:6][C:5]=1[CH3:30]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 336431-Iodopropane2×HCID 58937082HCID 58937082, compound

Product 2

HCID 58937082HCID 58937082, compoundYield 58%HCID 58937189HCID 58937189, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
56 °C

Procedure

A mixture of 5-[(4′-hydroxy-biphenyl-4-yl)-propyl-sulfamoyl]-2-methyl-benzoic acid methyl ester (100 mg, 0.25 mmol), 1-iodopropane (36.7 μl, 0.38 mmol) and potassium carbonate (52 mg, 38 mmol) in 5 ml acetone was heated at 56° C. under nitrogen overnight. Additional 1-iodopropane was added (35.7 μl, 0.38 mmol) and the mixture was heated at 56° C. under nitrogen overnight. The reaction mixture was then cooled to room temperature and diluted with 40 ml ethyl acetate. The ethyl acetate solution was washed sequentially with 30 ml water and 30 ml brine, dried (anhydrous sodium sulfate) and concentrated under reduced pressure. The residue was purified by preparative thick layer chromatography (silica gel), eluting with 3:1 toluene/ethyl acetate to yield the title compound as an off-white solid (21 mg, 17% yield) along with 5-[(4′-hydroxy-biphenyl-4-yl)-propyl-sulfamoyl]-2-methyl-benzoic acid methyl ester (64 mg, 58% yield).

Workup

  1. temperaturethe mixture was heated at 56° C. under nitrogen overnight
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. washThe ethyl acetate solution was washed sequentially with 30 ml water and 30 ml brine
  4. dry with materialdried (anhydrous sodium sulfate)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by preparative thick layer chromatography (silica gel)
  7. washeluting with 3:1 toluene/ethyl acetate

Sources & evidence

ORD record
ord-1c8b4f1bc7f34787b9f906b7339b202d
Source dataset
uspto-grants-2007_08
Patent number
US07262318B2

Reaction notes

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