Sodium Azide → N-acetyl-4-azido-L-proline ethyl ester

HRID 1723901Notes

Reaction equation

HRID 1723901 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[CH2:5]([O:7][C:8](=[O:22])[C@@H:9]1[CH2:13][CH:12](OS(C)(=O)=O)[CH2:11][N:10]1[C:19](=[O:21])[CH3:20])[CH3:6]>CN(C=O)C>[CH2:5]([O:7][C:8](=[O:22])[C@@H:9]1[CH2:13][CH:12]([N:1]=[N+:2]=[N-:3])[CH2:11][N:10]1[C:19](=[O:21])[CH3:20])[CH3:6]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 86601300N-acetyl-4-mesyloxy-L-proline ethyl ester

Product 1

HCID 86601301N-acetyl-4-azido-L-proline ethyl esterYield 99.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

243 g of sodium azide was added to a solution of 802 g of N-acetyl-4-mesyloxy-L-proline ethyl ester and 2.4 L of DMF, and the mixture was reacted at an inner temperature of 70° C. for 7 hours. The reaction solution was cooled, poured into ice water (4.8 L), and extracted with chloroform (3.2 L). The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure to obtain 644 g of N-acetyl-4-azido-L-proline ethyl ester as an oil.

Workup

  1. customthe mixture was reacted at an inner temperature of 70° C. for 7 hours
  2. temperatureThe reaction solution was cooled
  3. extractionextracted with chloroform (3.2 L)
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-586d54e2122745d09168a9b1fa7e8c8c
Source dataset
uspto-grants-2009_02
Patent number
US07485665B2

Reaction notes

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