Methyl iodide → methyl N-(tert-butoxycarbonyl)-N-(2-cyanoethyl)-2-methylalaninate

HRID 1479039Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1479039
[CH3:1]I.[C:3]([O:7][C:8]([N:10]([CH2:17][CH2:18][C:19]#[N:20])[C:11]([CH3:16])([CH3:15])[C:12]([OH:14])=[O:13])=[O:9])([CH3:6])([CH3:5])[CH3:4]>CN(C=O)C>[C:3]([O:7][C:8]([N:10]([CH2:17][CH2:18][C:19]#[N:20])[C:11]([CH3:15])([CH3:16])[C:12]([O:14][CH3:1])=[O:13])=[O:9])([CH3:6])([CH3:5])[CH3:4]

Komponenten

4

Edukt 2

HCID 6328Methyl iodideHCID 575236442-((tert-Butoxycarbonyl)(2-cyanoethyl)amino)-2-methylpropanoic acid

Produkt 1

HCID 57523645methyl N-(tert-butoxycarbonyl)-N-(2-cyanoethyl)-2-methylalaninateAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Methyl iodide (12.5 mL, 193.2 mmol) was added to a mixture of 2-[(tert-butoxycarbonyl)(2-cyanoethyl)amino]-2-methylpropanoic acid (16.5 g, 64.4 mmol) and KHCO3 (12.9 g, 193.2 mmol) in DMF (150 mL) and the reaction mixture was stirred at room temperature for 16 hours. After dilution with water, the solution was extracted with a 1/1 mixture of hexane/EA (2×). The combined organics were dried over magnesium sulfate and concentrated in vacuo to afford the title compound (16.5 g, 95%) as a yellow oil. 1H NMR (DMSO-d6) δ 3.61-3.55 (m, 5H), 2.71 (t, J=6.76 Hz, 2H), 1.42-1.36 (m, 15H).

Aufarbeitung

  1. extractionAfter dilution with water, the solution was extracted with a 1/1 mixture of hexane/EA (2×)
  2. dry with materialThe combined organics were dried over magnesium sulfate
  3. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-901456e0fd4c4dee8b6db89cdb067ac6
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09403835B2

Notizen zur Reaktion

Wird geladen…