Sodium Azide → Methyl(4S)-5-azido-4-[(tert-butoxy)carbonylamino]pentanoate

HRID 421592Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 421592
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:16]OS(C1C=CC(C)=CC=1)(=O)=O)[CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].[N-:28]=[N+:29]=[N-:30].[Na+]>CN(C=O)C>[N:28]([CH2:16][C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[N+:29]=[N-:30]

Komponenten

4

Edukt 2

HCID 33557Sodium AzideHCID 15933198Methyl(4S)-4-[(tert-butoxy)carbonylamino]-5-[(4-methylphenyl)sulfonyloxy]pentanoate

Produkt 1

HCID 10778574Methyl(4S)-5-azido-4-[(tert-butoxy)carbonylamino]pentanoateAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Methyl (4S)-4-[(tert-butoxy)carbonylamino]-5-[(4-methylphenyl) sulfonyloxy]pentanoate (4.93 mmol, 1.98 g) was dissolved in DMF (15 mL) and sodium azide (14.8 mmol, 0.961 g) were added. The reaction was heated at 50° C. for 3 hours. The reaction mixture was filtered and the solvent was removed in vacuo. The crude was purified by flash chromatography (SiO2, ethyl acetate) to yield the title compound (1.07 g, 80% yield). ES-MS: 273 (M+1).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent was removed in vacuo
  3. customThe crude was purified by flash chromatography (SiO2, ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-4e40cd648b90456fa22f5983687db31c
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101588B2

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