Iodoethane → N-[(1,1-Dimethylethoxy)carbonyl]-N-ethyl-L-alanine

HRID 1486097Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1486097
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH3:13])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:14](I)[CH3:15].[H-].[Na+]>C1COCC1>[C:1]([O:5][C:6]([N:8]([CH2:14][CH3:15])[C@@H:9]([CH3:13])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 85082Tert-butoxycarbonylalanine

Produkt 1

HCID 71423142N-[(1,1-Dimethylethoxy)carbonyl]-N-ethyl-L-alanineAusbeute 87,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of (S)-2-(tert-butoxycarbonylamino)propanoic acid (0.7 g, 3.7 mmol) and ethyl iodide (2.6 ml, 32.2 mmol) in THF (10 ml) was added sodium hydride (60% w/w dispersion in mineral oil, 576 mg, 14.4 mmol). The reaction was sealed and stirred at 60° C. overnight, then partitioned between EtOAc and H2O. The aqueous layer was acidified to pH 4 with citric acid solution and extracted with EtOAc. The organic layer was dried over MgSO4, filtered and concentrated to provide (S)-2-(tert-butoxycarbonyl(ethyl)amino)propanoic acid (700 mg, 87%) as an oil.

Aufarbeitung

  1. customThe reaction was sealed
  2. custompartitioned between EtOAc and H2O
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-3c9421c99ef048abab6d79f89116cb5b
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09422331B2

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