Reaktion #47613

Reaktionsgleichung

3-(2-chloro-phenoxy)-4-((S)-1-methoxycarbonyl-3-methylsulfanyl-propylamino)-but-2-enoic acid ethyl ester

→

(S)-2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methylsulfanyl-butyric acid methyl ester

Ausbeute 34.5%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter this time, the mixture was cooled to room temperature
2. 2
   Einengenconcentrated in vacuo with silica gel (4 g)
3. 3
   SonstigePurification by Biotage flash chromatography (Aspire 40 g column, 16% ethyl acetate/hexanes to 50% ethyl acetate/hexanes)

Vorschrift

A solution of 3-(2-chloro-phenoxy)-4-((S)-1-methoxycarbonyl-3-methylsulfanyl-propylamino)-but-2-enoic acid ethyl ester (1.56 g, 3.88 mmol) in acetonitrile (4 mL) was placed in a sealed microwave reaction tube and heated in a microwave reactor at 140° C. for 3 h. After this time, the mixture was cooled to room temperature and concentrated in vacuo with silica gel (4 g). Purification by Biotage flash chromatography (Aspire 40 g column, 16% ethyl acetate/hexanes to 50% ethyl acetate/hexanes) afforded (S)-2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methylsulfanyl-butyric acid methyl ester (477 mg, 24% over two steps) as a golden oil: HR-ES-MS m/z calculated for C16H18NO4ClS [M+Na]+ 378.0537, observed 378.0538.

Quelle