Lithium Hydroxide → N-((N-Methyl-N-((2-pyridinyl)methyl)amino)carbonyl)valine

HRID 2210944

Reaction equation

HRID 2210944 reaction equation
C[O:2][C:3](=[O:20])[C@H:4]([CH:17]([CH3:19])[CH3:18])[NH:5][C:6]([N:8]([CH3:16])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)=[O:7].[OH-].[Li+]>O1CCOCC1>[CH3:16][N:8]([C:6]([NH:5][C@H:4]([C:3]([OH:20])=[O:2])[CH:17]([CH3:19])[CH3:18])=[O:7])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 10039258(S)-3-Methyl-2-[[methyl-(2-pyridinylmethyl)amino]carbonyl]aminobutyric acid methyl ester

Product 1

HCID 10106914N-((N-Methyl-N-((2-pyridinyl)methyl)amino)carbonyl)valineYield 85%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 4.47 g (16 mmol) of N-((N-methyl-N-((2-pyridinyl)methyl)amino)carbonyl)valine methyl ester in 65 ml of dioxane was treated with 65 ml of 0.5M aqueous lithium hydroxide. After being stirred at ambient temperature for 1 h, the resulting solution was concentrated in vacuo to a small volume (ca. 5 ml), neutralized to pH 5 with 1M aqueous HCl, and extracted with three 100 ml portions of ethyl acetate. The combined organic layers were dried over Na2SO4 and concentrated in vacuo to provide 3.61 g (85%) of the desired compound as an oil.

Workup

  1. concentrationthe resulting solution was concentrated in vacuo to a small volume (ca. 5 ml)
  2. extractionextracted with three 100 ml portions of ethyl acetate
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f8bc01dbc26345a19e81793a8b8bf34b
Source dataset
uspto-grants-1995_10
Patent number
US05461067

Linked notes

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