Reaktion #462152

ord-3c7112c140fd452e977e1d60b3165b4b

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 ethyl acetate/hexane

Vorschrift

A solution of N-benzyloxycarbonyl 3 (S)-amino-1,2-(S)-epoxy-4-phenylbutane (30.1 g, 0.10 mol) and 165mL 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 ethyl acetate/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: US05482947uspto-grants-1996_01