Triethylamine → HCID 22679035, compound

HRID 1837787Notes

Reaction equation

HRID 1837787 reaction equation
[CH3:1][C:2]([NH:7][C:8](=O)[CH:9]([O:11][N:12]1[C:17]([CH3:19])([CH3:18])[CH2:16][CH2:15][CH2:14][C:13]1([CH3:21])[CH3:20])[CH3:10])([CH3:6])[C:3]([OH:5])=[O:4].C(N(CC)CC)C.ClC(OCC)=O>CC(C)=O>[CH3:1][C:2]1([CH3:6])[C:3](=[O:4])[O:5][C:8]([CH:9]([O:11][N:12]2[C:13]([CH3:20])([CH3:21])[CH2:14][CH2:15][CH2:16][C:17]2([CH3:18])[CH3:19])[CH3:10])=[N:7]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 22679034HCID 22679034, compound

Product 1

HCID 22679035HCID 22679035, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred mixture of 2-methyl-2-[2-(2,2,6,6-tetramethylpiperidin-1-yloxy)-propionylamino]-propionic acid (0.50 g; 0.0016 mol), triethylamine (0.16 g, 0.0016 mol) and acetone (5 ml) there was added ethyl chloroformate (0.17 g; 0.0016 mol). After 2 hours, the mixture was filtered and the filtrate was concentrated under vacuum. The residue was mixed with hexane (5 ml) and the solution was decanted from the precipitated solid. The decanted solution was concentrated under vacuum to give 0.30 g (64% yield) of 4,4-dimethyl-2-[1-(2,2,6,6-tetramethylpiperidin-1-yloxy)-ethyl]4H-oxazol-5-one (AzTEMPO) as a yellow oil.

Workup

  1. filtrationthe mixture was filtered
  2. concentrationthe filtrate was concentrated under vacuum
  3. additionThe residue was mixed with hexane (5 ml)
  4. customthe solution was decanted from the precipitated solid
  5. concentrationThe decanted solution was concentrated under vacuum

Sources & evidence

ORD record
ord-fcf15c8676854c9585ebebaf09392612
Source dataset
uspto-grants-2004_08
Patent number
US06784264B2

Reaction notes

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