Hydrochloric Acid → Diethyl 3-(2-(2-aminoethoxy)ethoxy)-1,1-difluoropropylphosphonate hydrochloride

HRID 2407853Notes

Reaction equation

HRID 2407853 reaction equation
[N:1]([CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][C:12]([P:15](=[O:22])([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18])([F:14])[F:13])=[N+]=[N-].[ClH:23].CCOCC>CCO.[OH-].[Pd+2].[OH-]>[ClH:23].[NH2:1][CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][C:12]([P:15](=[O:22])([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18])([F:14])[F:13]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 86678262Diethyl 3-(2-(2-azidoethoxy)ethoxy)-1,1-difluoropropylphosphonate

Product 1

HCID 86678263Diethyl 3-(2-(2-aminoethoxy)ethoxy)-1,1-difluoropropylphosphonate hydrochloride

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a solution of diethyl 3-(2-(2-azidoethoxy)ethoxy)-1,1-difluoropropylphosphonate (1 eq) in EtOH (2 M) solution was added palladium hydroxide (0.05 eq) and 2 M HCl in ether (1.1 eq). The reaction mixture was stirred under hydrogen (1 atm) overnight. The palladium was filtered off and the filtrate was concentrated en vaccuo. The crude mixture was used for the next reaction without further purification.

Workup

  1. filtrationThe palladium was filtered off
  2. concentrationthe filtrate was concentrated en vaccuo
  3. customThe crude mixture was used for the next reaction without further purification

Sources & evidence

ORD record
ord-ac1134653a724b8fbab12a99c9212076
Source dataset
uspto-grants-2014_08
Patent number
US08808703B2

Reaction notes

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