Water → Tert-butyl (2-(2-azidoethoxy)ethyl)carbamate

HRID 431452Notes

Reaction equation

CS(O[CH2:6][CH2:7][O:8][CH2:9][CH2:10][NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])(=O)=O.[N-:19]=[N+:20]=[N-:21].[Na+].O>CN(C)C=O>[N:19]([CH2:6][CH2:7][O:8][CH2:9][CH2:10][NH:11][C:12](=[O:13])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[N+:20]=[N-:21]

Participants

Conditions

Temperature: 90 °C

Procedure

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.

Workup

temperaturethe solution was cooled to room temperature
extractionThe reaction mixture was then extracted with Et2O (3×300 mL)
washThe combined organic extracts were washed with H2O (4×100 mL) and brine (2×100 mL)
dry with materialThe organic portion was dried over MgSO4
concentrationconcentrated

Sources & evidence

ORD record: ord-6d65a457cd1d42d1b364a684d83f8e76
Source dataset: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06660735B2

Reaction notes

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