Azido-PEG3-phosphonic acid ethyl ester → Diethyl 2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethylphosphonate

HRID 2205007Notes

Reaction equation

HRID 2205007 reaction equation
[N:1]([CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][P:15](=[O:22])([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18])=[N+]=[N-]>CCO.[OH-].[OH-].[Pd+2]>[NH2:1][CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][P:15](=[O:22])([O:16][CH2:17][CH3:18])[O:19][CH2:20][CH3:21]

Participants

4

Reactant 1

HCID 86678293Azido-PEG3-phosphonic acid ethyl ester

Product 1

HCID 86667767Diethyl 2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethylphosphonate

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a solution of diethyl 2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethylphosphonate (1 eq) in EtOH (0.1 M) was added Pd(OH)2 (0.05 eq). The reaction mixture was stirred under hydrogen (1 atm) for 4 hours. The mixture was filtered through Celite and washed with MeOH. The solvent was removed en vaccuo. The crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-10% MeOH/DCM with 0.5% NH3 to give the product 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-b62c51cb36ce427b941e125baeefea94
Source dataset
uspto-grants-2016_06
Patent number
US09365506B2

Reaction notes

Loading…