HCID 54757662, compound → 4-Chloro-N-(3-((2-hydroxy-4-oxocyclopent-2-en-1-yl)methyl)phenethyl)benzenesulfonamide

HRID 41144Notes

Reaction equation

HRID 41144 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][CH:21]3[CH2:25][C:24]([O:26]CC(C)C)=[CH:23][C:22]3=[O:31])[CH:15]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1>CC(C)=O.Cl.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][CH:21]3[CH2:25][C:24](=[O:26])[CH:23]=[C:22]3[OH:31])[CH:15]=2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 1

HCID 54757662HCID 54757662, compound

Product 1

HCID 546698474-Chloro-N-(3-((2-hydroxy-4-oxocyclopent-2-en-1-yl)methyl)phenethyl)benzenesulfonamideYield 88%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

A mixture of 32 (0.018 g, 0.04 mmol) in acetone (0.5 mL) and 2 N hydrochloric acid (0.2 mL) was stirred at rt for 6 h. The reaction mixture was diluted with water and the acetone was evaporated under reduced pressure. The aqueous phase was extracted with ethyl acetate and the combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated. The residue was purified by reverse phase preparative HPLC to provide the desired compound as a white solid. Yield: 88%.

Workup

  1. customthe acetone was evaporated under reduced pressure
  2. extractionThe aqueous phase was extracted with ethyl acetate
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-71ec18cbd936433b836776daa22091ff
Source dataset
uspto-grants-2013_09
Patent number
US08530520B2

Reaction notes

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