Ethyl Acetoacetate → (R)-3-Azido-2-methylpropanoic acid, methyl ester

HRID 1360176Notes

Reaction equation

HRID 1360176 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C@H:4]([CH3:11])[CH2:5]OS(C)(=O)=O.[N-:13]=[N+:14]=[N-:15].[Na+].C(OC(=O)CC(C)=O)C>CN(C)C=O>[CH3:1][O:2][C:3](=[O:12])[C@H:4]([CH3:11])[CH2:5][N:13]=[N+:14]=[N-:15]

Participants

5

Reactant 3

HCID 8868Ethyl AcetoacetateHCID 33557Sodium AzideHCID 86621909methyl (2R)-2-methyl-3-[(methylsulfonyl)oxy]propanoate

Product 1

HCID 150729(R)-3-Azido-2-methylpropanoic acid, methyl esterYield 32%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(R)-3-methanesulfonyloxy-2-methyl-propionic acid methyl ester was dissolved in 100 mL of dimethylformamide, and then 8.2 g (126 mmol) of sodium azide was added thereto at 60° C., followed by stirring for 24 hours. After addition of 400 mL of ethylacetoacetate and washing with water, an organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and then the residue was purified by column chromatography to give 2 g (13.9 mmol) of the title compound in a yield of 32%.

Workup

  1. customat 60° C.
  2. washwashing with water
  3. dry with materialan organic layer was dried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-8e5757f8552a4b57b3ab41457b33320a
Source dataset
uspto-grants-2011_02
Patent number
US07879848B2

Reaction notes

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