Sodium Hydroxide → 6-(5-(2-(4-Fluorobenzenesulphonylamino)ethyl)-N-methylpyrrol-2-yl)-6-(3-pyridyl)hexanoic acid

HRID 487322Notes

Reaction equation

HRID 487322 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][C:14]2[N:18]([CH3:19])[C:17]([C:20]([C:28]3[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=3)=[CH:21][CH2:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26])=[CH:16][CH:15]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH-].[Na+].[H][H]>CO.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][C:14]2[N:18]([CH3:19])[C:17]([CH:20]([C:28]3[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=3)[CH2:21][CH2:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26])=[CH:16][CH:15]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 542116936-(5-(2-(4-fluorobenzenesulphonylamino)ethyl)-N-methyl-pyrrol-2-yl)-6-(3-pyridyl)hex-5-enoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 150570256-(5-(2-(4-Fluorobenzenesulphonylamino)ethyl)-N-methylpyrrol-2-yl)-6-(3-pyridyl)hexanoic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2.36 g of 6-(5-(2-(4-fluorobenzenesulphonylamino)ethyl)-N-methyl-pyrrol-2-yl)-6-(3-pyridyl)hex-5-enoic acid, 0.4 g of sodium hydroxide and 1 g of 10% palladium/charcoal in 50 ml of methanol is hydrogenated under 5 bar of hydrogen pressure. Then the catalyst is filtered off, the filtrate is evaporated down, the residue is diluted with water, acidified and extracted with ethylene chloride. The organic extract is evaporated down and the residue recrystallised from ethyl acetate.

Workup

  1. filtrationThen the catalyst is filtered off
  2. customthe filtrate is evaporated down
  3. additionthe residue is diluted with water
  4. extractionextracted with ethylene chloride
  5. extractionThe organic extract
  6. customis evaporated down
  7. customthe residue recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-cea8c83a55c14d0b8dcee5ffc1ab1f2f
Source dataset
uspto-grants-1994_03
Patent number
US05294626

Reaction notes

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