Sodium Hydroxide → HCID 10410915, compound

HRID 1494075Notes

Reaction equation

HRID 1494075 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH:15]([CH2:23][CH2:24][C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)[CH2:16][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][CH:15]([CH2:23][CH2:24][C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)[CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10343879HCID 10343879, compound

Product 1

HCID 10410915HCID 10410915, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 0.083 g (0.18 mmol) of methyl 8-(p-chlorophenylsulfonamido)-5-[2-(3-pyridyl)ethyl]-octanoate, 2 mL dioxane and 0.4 mL (0.4 mmol) 1N aqueous sodium hydroxide is stirred for 16 hours at room temperature. The solvent is evaporated and the residue taken up in water and the pH is adjusted to 5. The aqueous mixture is then extracted with methylene chloride (4×10 mL). Combined organic extract is dried (MgSO4), filtered and evaporated to give an oil which is crystallized from ether to give 8-(p-chlorophenylsulfonamido)-5-[2-(3-pyridyl)ethyl]-octanoic acid, m.p. 83-85°.

Workup

  1. customThe solvent is evaporated
  2. extractionThe aqueous mixture is then extracted with methylene chloride (4×10 mL)
  3. extractionCombined organic extract
  4. dry with materialis dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customto give an oil which
  8. customis crystallized from ether

Sources & evidence

ORD record
ord-92f826d0da94469c8153c2197a84427d
Source dataset
uspto-grants-1991_06
Patent number
US05025025

Reaction notes

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