Dimethylformamide → Methyl 3-azido-2-methylpropanoate

HRID 1360161Notes

Reaction equation

HRID 1360161 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[CH2:5]([O:7][C:8](=[O:13])[CH2:9][C:10](C)=O)C.[CH3:14]N(C)C=O>>[CH3:5][O:7][C:8](=[O:13])[C@@H:9]([CH3:14])[CH2:10][N:1]=[N+:2]=[N-:3]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 8868Ethyl AcetoacetateHCID 33557Sodium Azide

Product 1

HCID 154015Methyl 3-azido-2-methylpropanoateYield 96%

Conditions

Temperature
60 °C

Procedure

4.97 g (25.3 mmol) of (S)-3-methanesulfonyloxy-2-methyl-propionic acid methyl ester obtained in the above step (2) was dissolved in 40 mL of dimethylformamide, and then 5 g (76.8 mmol) of sodium azide was added thereto, followed by stirring at 60° C. for 24 hours. 200 mL of ethylacetoacetate was added to the solution, and the reaction solution was washed with water, then an organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, then the residue was purified by column chromatography to give 3.5 g (24.4 mmol) of the title compound in a yield of 96%.

Workup

  1. washthe reaction solution was washed with water
  2. dry with materialan organic layer was dried over anhydrous magnesium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-6a449a7ad52647adb75baac89dc68098
Source dataset
uspto-grants-2011_02
Patent number
US07879848B2

Reaction notes

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