Sodium Azide → HCID 178454124, Verbindung

HRID 707424Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 707424
CS(O[C@H:6]1[CH2:9][C@H:8]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7]1)(=O)=O.[N-:18]=[N+:19]=[N-:20].[Na+]>CN(C=O)C.O>[C:14]([O:13][C:11](=[O:12])[NH:10][C@H:8]1[CH2:9][C@@H:6]([N:18]=[N+:19]=[N-:20])[CH2:7]1)([CH3:17])([CH3:16])[CH3:15]

Komponenten

5

Edukt 2

HCID 33557Sodium AzideHCID 178454136HCID 178454136, Verbindung

Produkt 1

HCID 178454124HCID 178454124, VerbindungAusbeute 95,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To a solution of trans-3-((tert-butoxycarbonyl)amino)cyclobutyl methanesulfonate (29 g, 109 mmol) in DMF (100 mL) was added sodium azide (5.68 mL, 162 mmol, Sigma-Aldrich Chemical Company, Inc.) portionwise and the mixture stirred at 85° C. for 18 h. The reaction was diluted with water (200 mL) after cooling and extracted with EtOAc (3×100 mL). The combined organic was washed with water (2×100 mL) and brine, dried over Na2SO4 and evaporated in vacuo to give product tert-butyl(cis-3-azidocyclobutyl)carbamate (22 g, 104 mmol, 95% yield) that was used in the next step without further purification.

Aufarbeitung

  1. temperatureafter cooling
  2. extractionextracted with EtOAc (3×100 mL)
  3. washThe combined organic was washed with water (2×100 mL) and brine
  4. dry with materialdried over Na2SO4
  5. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5e6151cafec44b85b62538c10f2dd0b6
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09174992B2

Notizen zur Reaktion

Wird geladen…