Reaktion #82516

ord-e3445cf91de6468cba1bfd93db043cdd

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

A solution of N-benzyloxycarbonyl 3(S)-amino-1,2-(S)-epoxy-4-phenylbutane (30.1 g, 0.10 mol) and 165 mL 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: US05622949uspto-grants-1997_04