Sodium Hydroxide → 8-(4-Chloro-benzenesulfonylamino)-4-[2-(pyridin-3-yloxy)-ethyl]-octanoic acid

HRID 465558Notes

Reaction equation

HRID 465558 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][O: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:3]=[CH:4][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([CH2:23][CH2:24][O: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:10])=[O:9])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10027654Methyl 8-(p-chlorophenylsulfonamido)-4-[2-(3-pyridyloxy)ethyl]-octanoate

Product 1

HCID 103217648-(4-Chloro-benzenesulfonylamino)-4-[2-(pyridin-3-yloxy)-ethyl]-octanoic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 0.815 g of methyl 8-(p-chlorophenylsulfonamido)-4-[2-(3-pyridyloxy)ethyl]-octanoate in 13 ml dioxane is added 3.5 ml of 1N aqueous sodium hydroxide. The solution is stirred at room temperature for 60 h and then the solvent is evaporated. The residue is dissolved in water, the solution is adjusted to pH=6.5 and extracted with methylene chloride (3×20 ml). The combined organic extracts are dried, filtered and evaporated to yield an oil which is crystallized from ether to obtain 8-(p-chlorophenylsulfonamido)-4-[2-(3-pyridyloxy)ethyl]-octanoic acid, m.p. 77°-79°. Two further crystallizations from acetonitrile raise m.p. to 89°-91°.

Workup

  1. customthe solvent is evaporated
  2. dissolutionThe residue is dissolved in water
  3. extractionextracted with methylene chloride (3×20 ml)
  4. customThe combined organic extracts are dried
  5. filtrationfiltered
  6. customevaporated
  7. customto yield an oil which
  8. customis crystallized from ether

Sources & evidence

ORD record
ord-dd307c4714494cefa115ac8be190dd42
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

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