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

HRID 1723901Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1723901
[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]

Komponenten

4

Edukt 2

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

Produkt 1

HCID 86601301N-acetyl-4-azido-L-proline ethyl esterAusbeute 99,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-586d54e2122745d09168a9b1fa7e8c8c
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07485665B2

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