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

HRID 432714Notes

Reaction equation

HRID 432714 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

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 12106196tert-butyl N-{2-[2-(methanesulfonyloxy)ethoxy]ethyl}carbamate

Product 1

HCID 12106197Tert-butyl (2-(2-azidoethoxy)ethyl)carbamateYield 100.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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

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

Sources & evidence

ORD record
ord-b1e9a08fbe7a41a78c5b1df670e9fea8
Source dataset
uspto-grants-2003_12
Patent number
US06664265B2

Reaction notes

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