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

HRID 1603812

Reaktionsgleichung

Reaktionsgleichung von HRID 1603812
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

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

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 0.5 M 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 1 M 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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-d7c1361db56341af9b14c9f42df88b2a
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05990135

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