Sodium Hydroxide → HCID 10097261, compound

HRID 1885613Notes

Reaction equation

HRID 1885613 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([CH2:12][CH:13]([C:20](=[O:32])[N:21]([CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[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:32])[N:21]([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[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 11799781HCID 11799781, compound

Product 1

HCID 10097261HCID 10097261, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of methyl 5-(3,4-dichlorophenylsulfonyl)-4-(N,N-dipentylcarbamoyl)pentanoate (40.3 g) in ethanol (500 ml) was added a 2N sodium hydroxide solution (40 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 recrystallized from diethyl ether-hexane to give 38.2 g of 5-(3,4-dichlorophenylsulfonyl)-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 diethyl ether-hexane

Sources & evidence

ORD record
ord-40b98e78f79d48daa9d7ff7d6d5abe2f
Source dataset
uspto-grants-1992_09
Patent number
US05145869

Reaction notes

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