Sodium Hydroxide → HCID 9956704, compound

HRID 1645787Notes

Reaction equation

HRID 1645787 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][N:6]([CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[C:7]([CH:9]([CH2:16][S:17]([C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=1)(=[O:19])=[O:18])[CH2:10][CH2:11][C:12]([O:14]C)=[O:13])=[O:8].[OH-].[Na+]>C(O)C>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][N:6]([CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[C:7]([CH:9]([CH2:16][S:17]([C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=1)(=[O:18])=[O:19])[CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[O:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10648811HCID 10648811, compound

Product 1

HCID 9956704HCID 9956704, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of methyl 4-[N-(3-methoxypropyl)-N-pentylcarbamoyl]-5-(2-naphthylsulfonyl)pentanoate (2.50 g) in ethanol (30 ml) was added a 1N sodium hydroxide solution (5.1 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 ethyl acetate. The organic layer was washed with water, dried over MgSO4, and evaporated at reduced pressure. The residue was recrystallized from isopropyl ether to give 2.15 g of 4-[N-(3-methoxypropyl)-N-pentylcarbamoyl]-5-(2-naphthylsulfonyl)pentanoic acid.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. extractionextracted with ethyl acetate
  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 isopropyl ether

Sources & evidence

ORD record
ord-ded97b33bc284e4dac5738fbf319b0a9
Source dataset
uspto-grants-1993_01
Patent number
US05177069

Reaction notes

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