Sodium Hydroxide → (5RS)-5-Hydroxy-5-{6-[(1E)-(3RS)-3-hydroxy-1-undecenyl]-2-pyridyl}-pentanoic acid

HRID 977567Notes

Reaction equation

HRID 977567 reaction equation
C[O:2][C:3](=[O:27])[CH2:4][CH2:5][CH2:6][CH:7]([OH:26])[C:8]1[CH:13]=[CH:12][CH:11]=[C:10](/[CH:14]=[CH:15]/[CH:16]([OH:25])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[N:9]=1.[OH-].[Na+]>CO>[OH:26][CH:7]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10](/[CH:14]=[CH:15]/[CH:16]([OH:25])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[N:9]=1)[CH2:6][CH2:5][CH2:4][C:3]([OH:27])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15661711(5RS)-5-Hydroxy-5-{6-[(1E)-(3RS)-3-hydroxy-1-undecenyl]-2-pyridyl}-pentanoic acid methyl ester

Product 1

HCID 15661714(5RS)-5-Hydroxy-5-{6-[(1E)-(3RS)-3-hydroxy-1-undecenyl]-2-pyridyl}-pentanoic acidYield 92.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 140 mg of (5RS)-5-hydroxy-5-{6-[(1E)-(3RS)-3-hydroxy-1-undecenyl]-2-pyridyl}-pentanoic acid methyl ester in 6 ml of methanol is mixed with 6 ml of 0.5 n sodium hydroxide solution and stirred for 2 hours at room temperature. The methanol is removed in a vacuum, the residue is acidified to pH 4 with 0.5 n sulfuric acid, shaken out with ethyl acetate, the organic phase is dried on sodium sulfate and concentrated by evaporation. 125 mg of the title compound is thus obtained as colorless oil.

Workup

  1. customThe methanol is removed in a vacuum
  2. stirringshaken out with ethyl acetate
  3. customthe organic phase is dried on sodium sulfate
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-5d4cba57b8ce4078816f17e0179d5a21
Source dataset
uspto-grants-1997_03
Patent number
US05614634

Reaction notes

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