Sodium Hydroxide → HCID 10530264, compound

HRID 1645794Notes

Reaction equation

HRID 1645794 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]([CH2:14][CH:15]([C:22](=[O:38])[N:23]([CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH2:24][C:25]([N:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1)=[O:26])[CH2:16][CH2:17][C:18]([O:20]C)=[O:19])(=[O:13])=[O:12].[OH-].[Na+]>CO>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]([CH2:14][CH:15]([C:22](=[O:38])[N:23]([CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH2:24][C:25]([N:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1)=[O:26])[CH2:16][CH2:17][C:18]([OH:20])=[O:19])(=[O:13])=[O:12]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10650199HCID 10650199, compound

Product 1

HCID 10530264HCID 10530264, compoundYield 45.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 5-(2-naphthylsulfonyl)-4-(N-pentyl-N-piperidinocarbonylmethylcarbamoyl)pentanoate (0.18 g) in methanol (3 ml) was added a 1N sodium hydroxide solution (0.32 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 0.08 g of 5-(2-naphthylsulfonyl)-4-(N-pentyl-N-piperidinocarbonylmethylcarbamoyl)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-8f7671b3859c44388c17a390a477a7ea
Source dataset
uspto-grants-1993_01
Patent number
US05177069

Reaction notes

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