Sodium Azide → ethyl (2R)-4-azido-2-methyl-2-(methylsulfonyl)butanoate

HRID 2405905Notes

Reaction equation

HRID 2405905 reaction equation
Br[CH2:2][CH2:3][C@@:4]([CH3:14])([S:10]([CH3:13])(=[O:12])=[O:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6].[N-:15]=[N+:16]=[N-:17].[Na+]>CS(C)=O.CCOC(C)=O>[N:15]([CH2:2][CH2:3][C@@:4]([CH3:14])([S:10]([CH3:13])(=[O:12])=[O:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[N+:16]=[N-:17]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 86670635(R)-ethyl 4-bromo-2-methyl-2-(methylsulfonyl)butanoate

Product 1

HCID 86710224ethyl (2R)-4-azido-2-methyl-2-(methylsulfonyl)butanoate

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of ethyl (2R)-4-bromo-2-methyl-2-(methylsulfonyl)butanoate (4.5 g, 15.7 mmol, 1 eq) in DMSO (5 mL) was added sodium azide (1.02 g, 15.7 mmol, 1 eq). The mixture was heated at 80° C. for 3 h. The mixture was then diluted with EtOAc and washed with water. The organic layer was dried (MgSO4), filtered and concentrated to give ethyl (2R)-4-azido-2-methyl-2-(methylsulfonyl)butanoate which was used without further purification.

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8477307018c54c14bb9b7785630d73cd
Source dataset
uspto-grants-2014_08
Patent number
US08809333B2

Reaction notes

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