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

HRID 465561Notes

Reaction equation

HRID 465561 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 (=1.01 bar) pressure of hydrogen at room temperature for 48 h. 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-9e8c72bdc68942998bbaee967f15485e
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

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