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(R)-Benzyl 2-(3-((tert-butoxycarbonyl)amino)-2-oxopiperidin-1-YL)acetate → {(3R)-3-[(tert-Butoxycarbonyl)amino]-2-oxopiperidin-1-yl}acetic acid

HRID 417450
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 417450
C([O:8][C:9](=[O:26])[CH2:10][N:11]1[CH2:16][CH2:15][CH2:14][C@@H:13]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:12]1=[O:25])C1C=CC=CC=1.[H][H]>[Pd].C(O)C>[C:21]([O:20][C:18]([NH:17][C@@H:13]1[CH2:14][CH2:15][CH2:16][N:11]([CH2:10][C:9]([OH:26])=[O:8])[C:12]1=[O:25])=[O:19])([CH3:24])([CH3:22])[CH3:23]
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Komponenten

5

Edukt 2

HCID 66620011(R)-Benzyl 2-(3-((tert-butoxycarbonyl)amino)-2-oxopiperidin-1-YL)acetateHCID 178418361HCID 178418361, Verbindung2×

Produkt 1

HCID 51980104{(3R)-3-[(tert-Butoxycarbonyl)amino]-2-oxopiperidin-1-yl}acetic acidAusbeute 95,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702
Ethanol
Lösungsmittel

Versuchsvorschrift

Palladium on carbon (10%, 500 mg) was added to a solution of (R)-(3-tert-butoxycarbonylamino-2-oxo-piperidin-1-yl)-acetic acid benzyl ester (2.31 g, 6.37 mmol) in ethanol (50 mL). The atmosphere was replaced with hydrogen and maintained with a balloon filled with hydrogen and the above mixture was vigorously stirred. After 16 hours the hydrogen was removed and CELITE was added to the mixture with stirring and then the mixture was filtered though a pad of CELITE. The solvent was removed under reduced pressure and the resulting residue was azeotroped with toluene to provide (R)-(3-tert-butoxycarbonylamino-2-oxo-piperidin-1-yl)-acetic acid (1.65 g, 6.06 mmol, 95%). C12H20N2O5 calculated 272.3 observed [M+1]+ 271.2; rt=1.80 min.

Aufarbeitung

  1. temperaturemaintained with a balloon
  2. customAfter 16 hours the hydrogen was removed
  3. additionCELITE was added to the mixture
  4. stirringwith stirring
  5. filtrationthe mixture was filtered though a pad of CELITE
  6. customThe solvent was removed under reduced pressure
  7. customthe resulting residue was azeotroped with toluene

Quellen und Nachweise

ORD-Eintrag
ord-c935eef53f53430ab712a8bdf70aa0f9
Quelldatensatz
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08088368B2

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