Sodium Azide → Tert-butyl (2-(2-azidoethoxy)ethyl)carbamate

HRID 1245977Notes

Reaction equation

HRID 1245977 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].CS(O[CH2:10][CH2:11][O:12][CH2:13][CH2:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])(=O)=O>CN(C=O)C>[N:1]([CH2:10][CH2:11][O:12][CH2:13][CH2:14][NH:15][C:16](=[O:17])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[N+:2]=[N-:3]

Participants

4

Reactant 2

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

Product 1

HCID 12106197Tert-butyl (2-(2-azidoethoxy)ethyl)carbamateYield 97.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Under a nitrogen atmosphere, sodium azide (29.8 g, 458 mmol) was added to a solution of 2-{2-[(tert-butoxycarbonyl)amino]ethoxy}ethyl methanesulfonate (118 g, 416 mmol) in DMF, and the reaction was heated at 90° C. for six hours. The reaction was allowed to cool to room temperature overnight, and then the solvent was removed under reduced pressure. Water (1 L) was added, and the resulting solution was extracted with diethyl ether (4×500 mL). The combined extracts were washed with water (1×250 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure to yield 93.0 g of tert-butyl 2-(2-azidoethoxy)ethylcarbamate as a colorless oil.

Workup

  1. temperatureto cool to room temperature overnight
  2. customthe solvent was removed under reduced pressure
  3. additionWater (1 L) was added
  4. extractionthe resulting solution was extracted with diethyl ether (4×500 mL)
  5. washThe combined extracts were washed with water (1×250 mL)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-da35d29361334b20a54ef1bb4a2cf3d6
Source dataset
uspto-grants-2006_10
Patent number
US07125890B2

Reaction notes

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