Sodium Hydroxide → 3-[2-[(4-Chlorophenyl)sulphonylamino]ethyl]-5-[(4-fluorophenyl)methyl]benzenepropanoic acid

HRID 53333Notes

Reaction equation

HRID 53333 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][C:14]2[CH:15]=[C:16]([CH2:28][CH2:29][C:30]([O:32]CC)=[O:31])[CH:17]=[C:18]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)[CH:19]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][C:14]2[CH:15]=[C:16]([CH2:28][CH2:29][C:30]([OH:32])=[O:31])[CH:17]=[C:18]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)[CH:19]=2)(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19962373Ethyl 3-[2-[(4-chlorophenyl)sulphonylamino]ethyl]-5-[(4-fluorophenyl)methyl]benzenepropanoate

Product 1

HCID 98911343-[2-[(4-Chlorophenyl)sulphonylamino]ethyl]-5-[(4-fluorophenyl)methyl]benzenepropanoic acidYield 82.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of ethyl 3-[2-[(4-chlorophenyl)sulphonylamino]ethyl]-5-[(4-fluorophenyl)methyl]benzenepropanoate (500 mg), 2N sodium hydroxide solution (1.5 ml) and methanol (5 ml) was heated under reflux for 1 hour and then evaporated. The residue was dissolved in a small volume of water, and the solution was made acidic with 2N hydrochloric acid. The resulting mixture was extracted several times with ether and the combined extracts were dried (MgSO4) and evaporated to give the title compound,(390 mg), m.p. 85°-87° C. Found: C,60.78A H,5.06; N,2.87. C24H33ClFNO4S requires C,60.56; H,4.87; N,2.94%.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hour
  3. customevaporated
  4. dissolutionThe residue was dissolved in a small volume of water
  5. extractionThe resulting mixture was extracted several times with ether
  6. dry with materialthe combined extracts were dried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-01837250ab324f05a14ab0fe8ca15583
Source dataset
uspto-grants-1997_04
Patent number
US05618941

Reaction notes

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