Sodium Azide → 3-Azido-2-oxopropanoic acid

HRID 871065Notes

Reaction equation

HRID 871065 reaction equation
Br[CH2:2][C:3](=[O:7])[C:4]([OH:6])=[O:5].[N-:8]=[N+:9]=[N-:10].[Na+]>CS(C)=O>[N:8]([CH2:2][C:3](=[O:7])[C:4]([OH:6])=[O:5])=[N+:9]=[N-:10]

Participants

4

Reactant 2

HCID 33557Sodium Azide2×HCID 70684Bromopyruvic Acid

Product 1

HCID 866899443-Azido-2-oxopropanoic acid

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

KY-740 3-bromo-2-oxopropanoic acid (1.66 gr, 10 mmol) was added to a solution of sodium azide (0.715 gr, 11 mmol) in DMSO (20 ml) which was prepared by stirring the sodium azide in DMSO at room temperature for 40 min. the mixture reaction was stirred for 2 h at room temperature. It was quenched with water (50 ml). The mixture was extracted with Et2O (3×100 ml). The combined organic layers were washed with water, dried with Na2SO4, filtered, and concentrated in vacuo. Yield 1.1 gr (85%). 1HNMR (400 MHz, DMSO-d6) δ 6.3 (s, 2H). 13C-NMR δ 113.52, 136.31, 165.3.

Workup

  1. customwas prepared
  2. customthe mixture reaction
  3. customIt was quenched with water (50 ml)
  4. extractionThe mixture was extracted with Et2O (3×100 ml)
  5. washThe combined organic layers were washed with water
  6. dry with materialdried with Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dbae15518fb94f328349bfde9de3b5a7
Source dataset
uspto-grants-2015_03
Patent number
US08969573B2

Reaction notes

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