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

HRID 629952Notes

Reaction equation

HRID 629952 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 vacuo and the crude material was purified by flash chromatography on a COMBIFLASH™ system 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 vacuo
  4. customthe crude material was purified by flash chromatography on a COMBIFLASH™ system

Sources & evidence

ORD record
ord-228adc9c86b944f69a332c40b0886cc2
Source dataset
uspto-grants-2016_04
Patent number
US09315530B2

Reaction notes

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