Sodium Hydroxide → HCID 10506339, compound

HRID 1885616Notes

Reaction equation

HRID 1885616 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([CH2:12][CH:13]([C:20](=[O:35])[N:21]([CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:14][CH2:15][C:16]([O:18]C)=[O:17])(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8].[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([CH2:12][CH:13]([C:20](=[O:35])[N:21]([CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH2:22][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:14][CH2:15][C:16]([OH:18])=[O:17])(=[O:10])=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19879345HCID 19879345, compound

Product 1

HCID 10506339HCID 10506339, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of methyl 5-(3,4-dichlorophenylsulfonyl)-4-(N-pentyl-N-phenethylcarbamoyl)pentanoate (57 mg) in ethanol (1 ml) was added a 1N sodium hydroxide solution (0.12 ml). After stirring at room temperature for 16 hours, the reaction mixture was concentrated in vacuo, acidified with a dilute hydrochloric acid, and extracted with chloroform. The organic layer was washed with water, dried over MgSO4, and evaporated at reduced pressure. The residue was purified by preparative thin-layer chromatography on silica by developing with chloroform/ethanol (10:1) to give 45 mg of 5-(3,4-dichlorophenylsulfonyl)-4-(N-pentyl-N-phenethylcarbamoyl)pentanoic acid as an oil.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. extractionextracted with chloroform
  3. washThe organic layer was washed with water
  4. dry with materialdried over MgSO4
  5. customevaporated at reduced pressure
  6. customThe residue was purified by preparative thin-layer chromatography on silica

Sources & evidence

ORD record
ord-ccb0dd479c8145ecbec3359a09db66da
Source dataset
uspto-grants-1992_09
Patent number
US05145869

Reaction notes

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