Reaktion #42347

ord-1be4056efffd4947ba0508ca8c0247fe

Reaktionsgleichung

CC(C)CNC(=O)[C@H](C)N
N1-Isobutyl-L-alaninamide
CC(C)(C)OC(=O)N[C@@H](Cc1cc(F)cc(F)c1)[C@H]1CO1
tert-butyl (1S)-2-(3,5-difluorophenyl)-1-[(2S)-oxiran-2-yl]ethylcarbamate
→
CC(C)CNC(=O)C(C)NCC(O)C(Cc1cc(F)cc(F)c1)NC(=O)OC(C)(C)C
title compound
CC(C)CNC(=O)C(C)NCC(O)C(Cc1cc(F)cc(F)c1)NC(=O)OC(C)(C)C
[1-(3,5-Difluoro-benzyl)-2-hydroxy-3-(1-isobutylcarbamoyl-ethylamino)-propyl]-carbamic acid tert-butyl ester

Edukte

CC(C)CNC(=O)[C@H](C)N
N1-Isobutyl-L-alaninamide
CC(C)(C)OC(=O)N[C@@H](Cc1cc(F)cc(F)c1)[C@H]1CO1
tert-butyl (1S)-2-(3,5-difluorophenyl)-1-[(2S)-oxiran-2-yl]ethylcarbamate

Reagenzien

Keine

Lösungsmittel

CC(C)O
isopropanol

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturare refluxed 4 h
  2. 2
    TemperaturThe reaction is cooled
  3. 3
    Einengenconcentrated under reduced pressure
  4. 4
    SonstigePurification by flash column chromatography (silica, 8% methanol/chloroform)

Vorschrift

N1-Isobutyl-L-alaninamide (3.8 g, 26 mmol) and tert-butyl (1S)-2-(3,5-difluorophenyl)-1-[(2S)-oxiran-2-yl]ethylcarbamate prepared by the method in Example S-3 (3.1 g, 10.4 mmol) in isopropanol (50 mL) are refluxed 4 h. The reaction is cooled and concentrated under reduced pressure. Purification by flash column chromatography (silica, 8% methanol/chloroform) gives the title compound. ESI MS m/z 444.1 [M+H]+.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07727997B2uspto-grants-2010_06