N-(Benzyloxycarbonyl)aspartic acid → (S)-Benzyl (tetrahydro-2,5-dioxo-3-furyl)carbamate

HRID 356826

Reaktionsgleichung

Reaktionsgleichung von HRID 356826
[C:1]([NH:11][C@H:12]([C:17]([OH:19])=[O:18])[CH2:13][C:14]([OH:16])=O)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]>C(OC(=O)C)(=O)C>[CH2:4]([O:3][C:1]([NH:11][C@@H:12]1[C:17](=[O:18])[O:19][C:14](=[O:16])[CH2:13]1)=[O:2])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Komponenten

3

Edukt 1

HCID 2723942N-(Benzyloxycarbonyl)aspartic acid

Produkt 1

HCID 11128682(S)-Benzyl (tetrahydro-2,5-dioxo-3-furyl)carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7918Acetic AnhydrideLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

The above illustrated starting compound which is commercially available N-CBZ aspartic acid (205.7 g, 0.77 mol) was added to acetic anhydride (300 ml). This mixture was stirred at 75° C. for 4 hours. The excess acetic anhydride and acetic acid byproduct were distilled from the mixture under reduced pressure and the residue was recrystallised from hot dichloromethane. The product was collected by filtration, washed with hexane and dried at ambient temperature under reduced pressure to give a white fluffy solid.

Aufarbeitung

  1. distillationThe excess acetic anhydride and acetic acid byproduct were distilled from the mixture under reduced pressure
  2. customthe residue was recrystallised from hot dichloromethane
  3. filtrationThe product was collected by filtration
  4. washwashed with hexane
  5. customdried at ambient temperature under reduced pressure
  6. customto give a white fluffy solid

Quellen und Nachweise

ORD-Eintrag
ord-f220232a1ce74980bd2c13304127a203
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05840667

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