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

HRID 1494102Notes

Reaction equation

HRID 1494102 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 sodium hydroxide. The solution is stirred at room temperature for 60 hours 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°.

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-473df6268a0b49cba905f075222d1584
Source dataset
uspto-grants-1991_06
Patent number
US05025025

Reaction notes

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