Isoamylamine → n[3(s)-Benzyloxycarbonylamino-2(r)-hydroxy-4-phenylbutyl]n-isoamylamine

HRID 54238

Reaktionsgleichung

Reaktionsgleichung von HRID 54238
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C@@H:13]1[O:15][CH2:14]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:23]([NH2:28])[CH2:24][CH:25]([CH3:27])[CH3:26]>C(O)(C)C>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C@H:13]([OH:15])[CH2:14][NH:28][CH2:23][CH2:24][CH:25]([CH3:27])[CH3:26])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 7894IsoamylamineHCID 9861019(2S,3S)-1,2-Epoxy-3-(Cbz-amino)-4-phenylbutane

Produkt 1

HCID 10430124n[3(s)-Benzyloxycarbonylamino-2(r)-hydroxy-4-phenylbutyl]n-isoamylamineAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. temperatureto reflux for 2.5 hours
  2. concentrationconcentrated in vacuo
  3. customrecrystallized
  4. customThe product was isolated by filtration and from ethylacetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-e3445cf91de6468cba1bfd93db043cdd
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05622949

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