Sodium Hydroxide → HCID 10410915, compound

HRID 465532Notes

Reaction equation

HRID 465532 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 (example 8), 2 ml dioxane and 0.4 ml (0.4 mmol) 1N aqueous sodium hydroxide is stirred for 16 h 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-5de3cb61d5bc48c786c89ecb27fbaab9
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

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