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(2R)-2-azido-N-benzyl-3-hydroxypropanamide → (2R)-2-Amino-3-hydroxy-N-(phenylmethyl)propanamide

HRID 1852050
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1852050
[N:1]([C@H:4]([CH2:15][OH:16])[C:5]([NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6])=[N+]=[N-].[H][H]>C(OCC)(=O)C.[Pd]>[NH2:1][C@H:4]([CH2:15][OH:16])[C:5]([NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 56640203(2R)-2-azido-N-benzyl-3-hydroxypropanamideHCID 178418361HCID 178418361, Verbindung2×

Produkt 1

HCID 10655432(2R)-2-Amino-3-hydroxy-N-(phenylmethyl)propanamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
27.5 °C

Versuchsvorschrift

In an autoclave charged (2R)-2-azido-N-benzyl-3-hydroxypropanamide (68.0 gms) in ethyl acetate (680 ml). Charged catalyst 5% Pd-C (6.85 gms) and closed the autoclave. Applied 3.8 kg Hydrogen pressure maintaining temperature at 25-30° C. and maintained the reaction mixture at 25-30° C. for 1.0 hour. After completion of the reaction, released Hydrogen pressure and flushed the autoclave with Nitrogen gas. Filtered the reaction mass through hyflo bed and washed hyflo bed with ethyl acetate. Concentrated filtrate under reduced pressure at 30-35° C. till two volumes of ethyl acetate remains in the reaction mixture. Removed vacuum and cooled the reaction mass to 0-5° C. and maintained for 2.0 hours. The reaction mass was filtered and washed with cold ethyl acetate (2×40 ml). Dried the product (2R)-2-amino-N-benzyl-3-hydroxypropanamide under vacuum at 25-30° C. till constant weight.

Aufarbeitung

  1. customAfter completion of the reaction
  2. customflushed the autoclave with Nitrogen gas
  3. filtrationFiltered the reaction mass through hyflo bed
  4. washwashed
  5. customat 30-35° C.
  6. customRemoved vacuum
  7. temperaturecooled the reaction mass to 0-5° C.
  8. temperaturemaintained for 2.0 hours
  9. filtrationThe reaction mass was filtered
  10. washwashed with cold ethyl acetate (2×40 ml)
  11. dry with materialDried the product (2R)-2-amino-N-benzyl-3-hydroxypropanamide under vacuum at 25-30° C. till constant weight

Quellen und Nachweise

ORD-Eintrag
ord-086fcebc55394129afee68dbab3c5fc5
Quelldatensatz
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08957252B2

Notizen zur Reaktion

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