Dimethylformamide → HCID 22845730, compound

HRID 1885303Notes

Reaction equation

HRID 1885303 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[C@@H:5]1[CH2:9][CH:8](OS(C)(=O)=O)[CH2:7][N:6]1[CH2:15][CH3:16])[CH3:2].[N-:18]=[N+:19]=[N-:20].[Na+].CN(C=O)C>O>[CH2:1]([O:3][C:4](=[O:17])[C@@H:5]1[CH2:9][CH:8]([N:18]=[N+:19]=[N-:20])[CH2:7][N:6]1[CH2:15][CH3:16])[CH3:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 22845732HCID 22845732, compound

Product 1

HCID 22845730HCID 22845730, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3.50 g of N-ethyl-4-mesyloxy-L-proline ethylester, 1.54 g of sodium azide and 10 ml of DMF was reacted at an inner temperature of 90° C. for 4 hours and after cooling, the reaction mixture was poured into water and extracted with ethyl acetate. The extract was dried over magnesium sulfate and concentrated to obtain an oily product. This was purified by means of silica column chromatography to obtain 2.05 g of 4-azido-N-ethyl-L-proline ethylester.

Workup

  1. customwas reacted at an inner temperature of 90° C. for 4 hours
  2. temperatureafter cooling
  3. extractionextracted with ethyl acetate
  4. dry with materialThe extract was dried over magnesium sulfate
  5. concentrationconcentrated
  6. customto obtain an oily product
  7. customThis was purified by means of silica column chromatography

Sources & evidence

ORD record
ord-850bdce555564799b1448854a10d6af5
Source dataset
uspto-grants-1992_09
Patent number
US05143935

Reaction notes

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