Hydrazine → Aminooxy-PEG1-azide

HRID 928907Notes

Reaction equation

HRID 928907 reaction equation
[N:1]([CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][N:10]1C(=O)C2C(=CC=CC=2)C1=O)=[N+:2]=[N-:3].NN>CO>[N:1]([CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][NH2:10])=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 86678051HCID 86678051, compound

Product 1

HCID 58989132Aminooxy-PEG1-azideYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-(2-(2-azidoethoxy)ethoxy)isoindoline-1,3-dione (43 mg, 0.17 mmol) in 0.8 mL of methanol was added hydrazine (5.5 mg, 0.17 mmol), and the resulting mixture was allowed to stir at room temperature for 2 h. Solvent was removed under reduced pressure, the crude product was purified by silica gel column chromatography (hexanes: ethyl acetate 1:2) to afford O-(2-(2-azidoethoxy)ethyl)hydroxylamine (15 mg, 0.10 mmol, 60%) as colorless oil. 1H NMR (CDCl3, 500 MHz) δ (ppm): 3.38 (t, J=4.8 Hz, 2H), 3.65 (stack, 4H), 3.82 (t, J=4.2 Hz, 2H), 5.49 (s, br, 2H).

Workup

  1. customSolvent was removed under reduced pressure
  2. customthe crude product was purified by silica gel column chromatography (hexanes: ethyl acetate 1:2)

Sources & evidence

ORD record
ord-44cb1e5c4e5f46778ed46c7fcccfdfc1
Source dataset
uspto-grants-2016_03
Patent number
US09290791B2

Reaction notes

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