Hydrochloric Acid → HCID 14158729, compound

HRID 446696Notes

Reaction equation

HRID 446696 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][N:15]=[N+]=[N-])[CH3:2].Cl.[Cl-].C(OC(COCCOCCOCC[NH3+])=O)C>C(O)C.[Pd]>[NH2:15][CH2:14][CH2:13][O:12][CH2:11][CH2:10][O:9][CH2:8][CH2:7][O:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:18]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14158728Ethyl {2-[2-(2-azidoethoxy)ethoxy]ethoxy}acetateHCID 87309460HCID 87309460, compound

Product 1

HCID 14158729HCID 14158729, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of {2-[2-(2-Azido-ethoxy)-ethoxy]-ethoxy}-acetic acid ethyl ester (0.30 g, 1.15 mmol, 1 eq) in ethanol (7 mL) was added 1M HCl (2.30 mL, 2.30 mmol, 2 eq) and 30.0 mg of Pd/C (10%). The flask was then evacuated and filled with H2. The mixture was stirred under H2 atmosphere at room temperature until the starting material disappeared on the TLC plate and in mass spectra. The solution was filtered through celite and concentrated in vacuo to give a pale yellow syrup. The obtained 2-[2-(2-ethoxycarbonylmethoxy-ethoxy)-ethoxy]-ethyl-ammonium chloride can be stored at −18° C. for several months. Work-up to get the free amine should only be performed immediately before the next step. To obtain the free amine 350 mg (1.29 mmol) of the respective hydrochloride were dissolved in chloroform. The organic layer was washed with sat. aq K2CO3 and H2O, and the solvent was evaporated in vacuo at room temperature to give a colorless oil. Yield: 210 mg (0.89 mmol, 69%).

Workup

  1. customThe flask was then evacuated
  2. additionfilled with H2
  3. filtrationThe solution was filtered through celite and
  4. concentrationconcentrated in vacuo
  5. customto give a pale yellow syrup

Sources & evidence

ORD record
ord-e931ac69e8734e72b963e9bc0d3871e6
Source dataset
uspto-grants-2013_07
Patent number
US08481494B2

Reaction notes

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