8-(p-Chlorophenylsulfonamido)-4-[3-(3-pyridyl)-2-propenyl]-octanoic acid → Cgs 22652

HRID 1494106Notes

Reaction equation

HRID 1494106 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([CH2:22][CH:23]=[CH:24][C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)[CH2:17][CH2:18][C:19]([OH:21])=[O:20])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[H][H]>C(O)C.[Pd]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([CH2:22][CH2:23][CH2:24][C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)[CH2:17][CH2:18][C:19]([OH:21])=[O:20])(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 536622708-(p-Chlorophenylsulfonamido)-4-[3-(3-pyridyl)-2-propenyl]-octanoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 131717Cgs 22652

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 34 mg of 8-(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)-2-propenyl]octanoic acid in 2 mL of ethanol is added 5 mg of 10% palladium on carbon. The mixture is hydrogenated at 1 atmosphere pressure of hydrogen at room temperature for 48 hours. Then the mixture is filtered, washed and evaporated to give an oil which is purified by preparative thin layer chromatography using petroleum ether, ethyl acetate, acetic acid (80:18:2) as solvent to yield 8-(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)propyl]-octanoic acid of Example 5a.

Workup

  1. filtrationThen the mixture is filtered
  2. washwashed
  3. customevaporated
  4. customto give an oil which
  5. customis purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-7c7df93eb0c84b11bcb599c5e69e606c
Source dataset
uspto-grants-1991_06
Patent number
US05025025

Reaction notes

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