Reaktion #518634

Reaktionsgleichung

H2O

2-{2-[(tert-butoxycarbonyl)amino]ethoxy}ethyl methanesulfonate

NaN3

→

tert-butyl 2-(2-azidoethoxy)ethylcarbamate

Ausbeute 100.8%

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe solution was cooled to room temperature
2. 2
   ExtraktionThe reaction mixture was then extracted with Et2O (3×300 mL)
3. 3
   WaschenThe combined organic extracts were washed with H2O (4×100 mL) and brine (2×100 mL)
4. 4
   TrocknenThe organic portion was dried over MgSO4
5. 5
   Einengenconcentrated

Vorschrift

A stirred solution of 2-{2-[(tert-butoxycarbonyl)amino]ethoxy}ethyl methanesulfonate (63.5 g, 0.224 mol) in 400 mL of N,N-dimethylformamide (DMF) was treated with NaN3 (16.1 g, 0.247 mol) and the reaction mixture was heated to 90° C. under N2. After 5 h, the solution was cooled to room temperature and treated with 500 mL of cold H2O. The reaction mixture was then extracted with Et2O (3×300 mL). The combined organic extracts were washed with H2O (4×100 mL) and brine (2×100 mL). The organic portion was dried over MgSO4 and concentrated to give 52.0 g of tert-butyl 2-(2-azidoethoxy)ethylcarbamate as a light brown oil.

Quelle