Azido-PEG2-Phosphonic Ester → Diethyl 2-(2-(2-aminoethoxy)ethoxy)ethylphosphonate

HRID 2407859Notes

Reaction equation

HRID 2407859 reaction equation
[N:1]([CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][P:12](=[O:19])([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15])=[N+]=[N-].[H][H]>CCO.[OH-].[OH-].[Pd+2]>[NH2:1][CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][P:12](=[O:19])([O:13][CH2:14][CH3:15])[O:16][CH2:17][CH3:18]

Participants

5

Reactant 2

HCID 86667776Azido-PEG2-Phosphonic EsterHCID 178418361HCID 178418361, compound

Product 1

HCID 86667777Diethyl 2-(2-(2-aminoethoxy)ethoxy)ethylphosphonate

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

Diethyl 2-(2-(2-azidoethoxy)ethoxy)ethylphosphonate (1 eq) was dissolved in EtOH (0.1 M). Pd(OH)2 (0.05 eq) was added to the reaction. Hydrogen gas was introduced via a balloon; and the reaction was stirred for 2 hours at room temperature. The mixture was filtered through Celite and washed with MeOH. The solvent was removed en vaccuo and the crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-10% MeOH/DCM with 0.5% NH3 to give diethyl 2-(2-(2-aminoethoxy)ethoxy)ethylphosphonate as a colorless oil.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washwashed with MeOH
  3. customThe solvent was removed en vaccuo
  4. customthe crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO)

Sources & evidence

ORD record
ord-7f6912ca993047e28918bae99b63f86f
Source dataset
uspto-grants-2014_08
Patent number
US08808703B2

Reaction notes

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