Hydrochloric Acid → Diethyl 3-(4-(2-aminoethyl)phenoxy)propylphosphonate

HRID 2407893Notes

Reaction equation

HRID 2407893 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:28]=[CH:27][C:16]([CH2:17][CH2:18][NH:19]C(=O)OC(C)(C)C)=[CH:15][CH:14]=1)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].Cl.O1CCOCC1>C(Cl)Cl>[NH2:19][CH2:18][CH2:17][C:16]1[CH:15]=[CH:14][C:13]([O:12][CH2:11][CH2:10][CH2:9][P:4](=[O:5])([O:3][CH2:1][CH3:2])[O:6][CH2:7][CH3:8])=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 86678287Tert-butyl 4-(3-(diethoxyphosphoryl)propoxy)phenethylcarbamate

Product 1

HCID 86678288Diethyl 3-(4-(2-aminoethyl)phenoxy)propylphosphonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(3-(diethoxyphosphoryl)propoxy)phenethylcarbamate (1 eq) in DCM (0.14 M) was added 4M HCl in dioxane (50 eq). The resulting mixture was stirred at room temperature for 2 hours. The mixture was concentrated en vaccuo. The crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-15% MeOH/DCM to give the product as a yellowish oil.

Workup

  1. concentrationThe mixture was concentrated en vaccuo
  2. customThe crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO)

Sources & evidence

ORD record
ord-437ec932b2a74bde83a50ede1fa3df84
Source dataset
uspto-grants-2014_08
Patent number
US08808703B2

Reaction notes

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