Water → (2R)-2-amino-2-ethoxycarbonylsuccinimide

HRID 426023Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 426023
C(OC([NH:11][C@:12]1([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:17][C:16](=[O:18])[NH:15][C:13]1=[O:14])=O)C1C=CC=CC=1.O.[H][H]>C(O)C.[Pd]>[NH2:11][C@:12]1([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:17][C:16](=[O:18])[NH:15][C:13]1=[O:14]

Komponenten

6

Edukt 3

HCID 962WaterHCID 9944916(R)-2-benzyloxycarbonylamino-2-ethoxycarbonylsuccinimideHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 10679104(2R)-2-amino-2-ethoxycarbonylsuccinimideAusbeute 86,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
35 °C

Versuchsvorschrift

(2R)-2-Benzyloxycarbonylamino-2-ethoxycarbonylsuccinimide (24.4 g, 76.2 mmol) in ethanol (73.2 ml) was heated at 60° C. to be dissolved and 5% Pd—C (2.71 g) and water (2.17 g) were added at 30-40° C. of inner temperature. After the atmosphere was substituted with nitrogen gas, hydrogen gas was introduced and the mixture was stirred at 30-40° C. for about 33 hours. When completion of the reaction was confirmed by HPLC, the reaction solution was filtered, the insoluble materials were washed with sprayed ethanol (20 ml×2) and the filtrate was concentrated. The resulting crystals were recrystallized from ethanol (24.4 ml) and the precipitated crystals were filtered, washed with sprayed ethanol (15 ml) and dried in vacuo at room temperature to give (2R)-2-amino-2-ethoxycarbonylsuccinimide (12.3 g). Yield 86.7%, HPLC 99.7%, Optical purity 100% e.e.

Aufarbeitung

  1. dissolutionto be dissolved
  2. additionwas introduced
  3. filtrationthe reaction solution was filtered
  4. washthe insoluble materials were washed with sprayed ethanol (20 ml×2)
  5. concentrationthe filtrate was concentrated
  6. customThe resulting crystals were recrystallized from ethanol (24.4 ml)
  7. filtrationthe precipitated crystals were filtered
  8. washwashed with sprayed ethanol (15 ml)
  9. customdried in vacuo at room temperature

Quellen und Nachweise

ORD-Eintrag
ord-c45dc7e4037340778813a13426803f2c
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08106230B2

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