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

HRID 32371Notes

Reaction equation

HRID 32371 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.CN(C=O)C.[N-:24]=[N+:25]=[N-:26].[Na+]>O>[N:24]([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+:25]=[N-:26]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 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 962WaterSolvent

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-dimethylformaniide (DMF) was treated with NaN3 (16.1 g, 0.247 mol) and the reaction mixture was heated to 90° C. under N2. After 5 hours, 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-9437f6bc26004298af949ebb2bb46fa2
Source dataset
uspto-grants-2008_09
Patent number
US07427629B2

Reaction notes

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