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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 79697
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 79697
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-69fc9ba8273c4c518bcd38c0b660e538
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08841278B2

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