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

HRID 465617Notes

Reaction equation

HRID 465617 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]([CH2:24][CH2:25][O:26][C:27]2[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=2)[CH2:17][CH2:18][C:19]([O:21]CC)=[O:20])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[Li+].[OH-].C(O)(=O)C>C(#N)C.O>[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]([CH2:24][CH2:25][O:26][C:27]2[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=2)[CH2:17][CH2:18][C:19]([OH:21])=[O:20])(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 3939Lithium HydroxideHCID 14986718Ethyl 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 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1.3 g (2.7 mmol) of ethyl 8-(p-chlorophenylsulfonamido)-4-[2-(3-pyridyloxy)ethyl]-octanoate in 8.1 ml acetonitrile is added 2.7 ml (5.4 mmol) 2M LiOH solution in water. After 18 h at room temperature, the reaction mixture is diluted with 9.5 ml water and filtered to remove a small amount of insoluble solid. The filtrate is acidified with 0.36 g (5.94 mmol) acetic acid and stirred in an ice bath. After 2 h the solid is filtered, washed with water and dried. Recrystallization from acetonitrile gives pure compound of example 31, namely 8-(p-chlorophenylsulfonamido)-4-[2-(3-pyridyloxy)ethyl)-octanoic acid, m.p. 86°-88°; further recrystallization gives m.p. 89°-91°. Compound forms potassium salt as hydrate (containing 1.5 moles water).

Workup

  1. filtrationfiltered
  2. customto remove a small amount of insoluble solid
  3. filtrationAfter 2 h the solid is filtered
  4. washwashed with water
  5. customdried
  6. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-3ac578bb4b104a508143a1611711b1fc
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

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