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

HRID 2204958Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2204958
[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]

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9942167Palladium hydroxideKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-4d1774b628094a10a0e57072dcb566ba
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09365506B2

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