Reaktion #86667

ord-4a43dbe2ee32438e853b9f525669c8c8

Reaktionsgleichung

COC(=O)[C@H](CCS(C)=O)NC(=O)OCc1ccccc1
Sulfoxide
COC(=O)[C@H](CCS(C)=O)NC(=O)OCc1ccccc1
(S)-2-Benzyloxycarbonylamino-4-methanesulfinyl-butyric acid methyl ester
→
C=C[C@H](NC(=O)OCc1ccccc1)C(=O)OC
(S)-2-Benzyloxycarbonylamino-but-3-enoic acid methyl ester

Edukte

COC(=O)[C@H](CCS(C)=O)NC(=O)OCc1ccccc1
Sulfoxide
COC(=O)[C@H](CCS(C)=O)NC(=O)OCc1ccccc1
(S)-2-Benzyloxycarbonylamino-4-methanesulfinyl-butyric acid methyl ester

Reagenzien

Keine

Lösungsmittel

CCOC(C)=O
EtOAc

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.DISTILLATIONheated/distilled at 140° C
  2. 2
    workup.DISTILLATIONThe distillate was purified by flash chromatography on silica using a gradient of EtOAc and (50/70) petroleum ether
  3. 3
    Sonstigeto yield a colourless oil, 0.905 g, 20%

Vorschrift

Sulfoxide 60 (5.69 g, 18.2 mmol) was placed in a round bottomed flask in a kugelrohr. This was directly connected to a low vacuum diaphragm pump and heated/distilled at 140° C. The distillate was purified by flash chromatography on silica using a gradient of EtOAc and (50/70) petroleum ether to yield a colourless oil, 0.905 g, 20%. Rf=0.24 (1/7 EtOAc/(50/70) petroleum ether).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09434762B2uspto-grants-2016_09