Sodium Hydroxide → Cgs 22652

HRID 465525Notes

Reaction equation

HRID 465525 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]([CH2:23][CH2:24][CH2:25][C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)[CH2:17][CH2:18][C:19]([O:21]C)=[O:20])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH-].[Na+]>O1CCOCC1>[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]([CH2:23][CH2:24][CH2:25][C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)[CH2:17][CH2:18][C:19]([OH:21])=[O:20])(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10479691Methyl 8-(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)-propyl]-octanoate

Product 1

HCID 131717Cgs 22652

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2.62 g (5.6 mmol) of methyl 8-(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)propyl]-octanoate in 14 ml dioxane is added 11.6 ml of 1N NaOH (11.6 mmol) and the mixture is heated at 60° for 2 h. The solvent is evaporated and the residue dissolved in water. The pH of the aqueous solution is adjusted to 5.0 using 2N aqueous HCl. The resulting mixture is extracted with methylene chloride (3×20 ml). The combined organic extract is dried (MgSO4), filtered and subjected to evaporation to give an oil. Crystallization from ether yields 8-(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)propyl]-octanoic acid, m.p. 114°-116°.

Workup

  1. temperaturethe mixture is heated at 60° for 2 h
  2. customThe solvent is evaporated
  3. dissolutionthe residue dissolved in water
  4. extractionThe resulting mixture is extracted with methylene chloride (3×20 ml)
  5. extractionThe combined organic extract
  6. dry with materialis dried (MgSO4)
  7. filtrationfiltered
  8. customsubjected to evaporation
  9. customto give an oil
  10. customCrystallization from ether

Sources & evidence

ORD record
ord-048bed388b284f6288e0a08af236fd07
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

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