6-(2-(4-Chlorobenzenesulphonylamino)indan-5-yl)-6-(3-pyridyl)hex-5-enoic acid → 3-Pyridinehexanoic acid, epsilon-(2-(((4-chlorophenyl)sulfonyl)amino)-2,3-dihydro-1H-inden-5-yl)-

HRID 487328Notes

Reaction equation

HRID 487328 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH:12]2[CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:21]([C:29]4[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=4)=[CH:22][CH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])[CH:18]=3)[CH2:13]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1>[OH-].[Na+].[Pd]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH:12]2[CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([CH:21]([C:29]4[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=4)[CH2:22][CH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])[CH:18]=3)[CH2:13]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 539382166-(2-(4-Chlorobenzenesulphonylamino)indan-5-yl)-6-(3-pyridyl)hex-5-enoic acid

Product 1

HCID 30770043-Pyridinehexanoic acid, epsilon-(2-(((4-chlorophenyl)sulfonyl)amino)-2,3-dihydro-1H-inden-5-yl)-

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 14798Sodium HydroxideSolvent

Procedure

3.0 g of 6-(2-(4-chlorobenzenesulphonylamino)indan-5-yl)-6-(3-pyridyl)hex-5-enoic acid are dissolved in 50 ml of 0.3N sodium hydroxide solution and hydrogenated with 1 g of palladium/charcoal at 40° C. and 3.5 bar for 12 hours. The catalyst is then removed by suction filtering and the filtrate is adjusted to pH 4 to 5. The product precipitated is separated off and taken up in chloroform. The organic extract is washed with water, dried and evaporated down. Then the mixture is chromatographed over a silica gel column using the eluant ethylene chloride/ethyl acetate/glacial acetic acid (70:30:2). The third fraction contains the desired product.

Workup

  1. customThe catalyst is then removed by suction
  2. filtrationfiltering
  3. customThe product precipitated
  4. customis separated off
  5. extractionThe organic extract
  6. washis washed with water
  7. customdried
  8. customevaporated down
  9. customThen the mixture is chromatographed over a silica gel column

Sources & evidence

ORD record
ord-e0d3ac6a97b9406995527e263ef4a673
Source dataset
uspto-grants-1994_03
Patent number
US05294626

Reaction notes

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