Reaktion #81939

ord-70465559ef8e43ae9e4252e327a48eef

Reaktionsgleichung

O=C(N[C@@H](Cc1ccccc1)[C@H]1CO1)OCc1ccccc1
N-benzyloxycarbonyl 3(S)-amino-1,2-(S)-epoxy-4-phenylbutane
CC(C)CCN
isoamylamine
→
CC(C)CCNC[C@@H](O)[C@H](Cc1ccccc1)NC(=O)OCc1ccccc1
N[3(S)-benzyloxycarbonylamino-2(R)-hydroxy-4-phenylbutyl]N-isoamylamine
Ausbeute 81.0%

Edukte

O=C(N[C@@H](Cc1ccccc1)[C@H]1CO1)OCc1ccccc1
N-benzyloxycarbonyl 3(S)-amino-1,2-(S)-epoxy-4-phenylbutane
CC(C)CCN
isoamylamine

Reagenzien

Keine

Lösungsmittel

CC(C)O
isopropyl alcohol

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturto reflux for 2.5 hours
  2. 2
    Einengenconcentrated in vacuo
  3. 3
    Sonstigerecrystallized
  4. 4
    SonstigeThe product was isolated by filtration and from ethylacetate/hexane

Vorschrift

Part C. A solution of N-benzyloxycarbonyl 3(S)-amino-1,2-(S)-epoxy-4-phenylbutane (30.1 g, 0.10 mol) and 165 mL of isoamylamine in 150 mL of isopropyl alcohol was heated to reflux for 2.5 hours. The solution was cooled to room temperature, concentrated in vacuo and then recrystallized. The product was isolated by filtration and from ethylacetate/hexane to afford 31.7 g (81%) of N[3(S)-benzyloxycarbonylamino-2(R)-hydroxy-4-phenylbutyl]N-isoamylamine.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05620977uspto-grants-1997_04