Reaktion #813084

ord-cb6e27112590467f85649ddbe83863d9

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 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 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: US05708004uspto-grants-1998_01