Sodium Hydroxide → 5-(4-acetylphenylsulfonyl)-4-(N,N-dipentylcarbamoyl)pentanoic acid

HRID 1885619Notes

Reaction equation

HRID 1885619 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([CH2:13][CH:14]([C:21](=[O:33])[N:22]([CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:15][CH2:16][C:17]([O:19]C)=[O:18])(=[O:12])=[O:11])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([S:10]([CH2:13][CH:14]([C:21](=[O:33])[N:22]([CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:15][CH2:16][C:17]([OH:19])=[O:18])(=[O:11])=[O:12])=[CH:8][CH:9]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19879344HCID 19879344, compound

Product 1

HCID 105762205-(4-acetylphenylsulfonyl)-4-(N,N-dipentylcarbamoyl)pentanoic acidYield 79.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 5-(4-acetylphenylsulfonyl)-4-(N,N-dipentylcarbamoyl)pentanoate (0.35 g) in methanol (15 ml) was added a 1N sodium hydroxide solution (1 ml). After stirring at room temperature for 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 recrystallized from dichloromethane-hexane to give 0.27 g of 5-(4-acetylphenylsulfonyl)-4-(N,N-dipentylcarbamoyl)pentanoic acid.

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 recrystallized from dichloromethane-hexane

Sources & evidence

ORD record
ord-d8c1a4fdd764403ab3392564fb67d247
Source dataset
uspto-grants-1992_09
Patent number
US05145869

Reaction notes

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