Sodium Hydroxide → Cgs 22652

HRID 1494069Notes

Reaction equation

HRID 1494069 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 hours. 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 hours
  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-9344de3493074d94b4b8e85642734ca2
Source dataset
uspto-grants-1991_06
Patent number
US05025025

Reaction notes

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