Methanol → (2S,3R)-methyl 3-amino-1-(tert-butyldimethylsilyl)-4-oxoazetidine-2-carboxylate

HRID 1783439Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1783439
[N:1]([C@H:4]1[C:7](=[O:8])[N:6]([Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])[C@@H:5]1[C:16]([O:18][CH3:19])=[O:17])=[N+]=[N-].CO>C(O)(C(F)(F)F)=O.[Pd].O1CCOCC1>[NH2:1][C@H:4]1[C:7](=[O:8])[N:6]([Si:9]([C:12]([CH3:14])([CH3:15])[CH3:13])([CH3:10])[CH3:11])[C@@H:5]1[C:16]([O:18][CH3:19])=[O:17]

Komponenten

6

Edukt 2

HCID 887MethanolHCID 57589884(2S,3R)-methyl 3-azido-1-(tert-butyldimethylsilyl)-4-oxoazetidine-2-carboxylate

Produkt 1

HCID 57589866(2S,3R)-methyl 3-amino-1-(tert-butyldimethylsilyl)-4-oxoazetidine-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6422Trifluoroacetic acidKatalysatorHCID 23938PalladiumKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of 132 (5.85 mmol) in 3:1 methanol:dioxane (25 mL) was added a few drops of TFA and 10% Pd/C (10 wt %). The reaction was stirred under atmospheric hydrogen for one hour and then filtered through Celite. The solvent was removed and the residue triturated with diethyl ether to afford 133, which was used in the next step without further purification.

Aufarbeitung

  1. filtrationfiltered through Celite
  2. customThe solvent was removed
  3. customthe residue triturated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-d28195f9c9524fe4962bc858c6a23a46
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07501404B2

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