Reaktion #2444243

Reaktionsgleichung

oxazolidine-amide

(R)-tert-Butyl 2,2,4-trimethyl-4-(2-(4-(octyloxy)-3-(trifluoromethyl)phenyl)-2-oxoethylcarbamoyl)oxazolidine-3-carboxylate

Lawesson's Reagent

→

(R)-tert-Butyl 2,2,4-trimethyl-4-(5-(4-(octyloxy)-3-(trifluoromethyl)phenyl)thiazol-2-yl)oxazolidine-3-carboxylate

Ausbeute 67.0%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas sealed
2. 2
   TemperaturAfter cooling to room temperature
3. 3
   Sonstigethe reaction mixture was purified by silica gel column chromatography

Vorschrift

A suspension of protected oxazolidine-amide 6 (180 mg, 1.0 equivalent) and Lawesson's Reagent (390 mg, 3.0 equivalents) in toluene (5 mL) was sealed and heated at 100° C. for 1 hour. After cooling to room temperature, the reaction mixture was purified by silica gel column chromatography using the Combi-Flash system (Hex:EtOAc) as a thick colourless oil in 67% yield (120 mg). TLC (1:2 EtOAc:Hex), Rf=0.8; MS (ESI, M+H+)=571.11; 1H NMR (400 MHz, CDCl3) δ 7.73 (br s, 1H), 7.70 (s, 1H), 7.61 (d, 1H, J=6.8 Hz), 7.01 (d, 1H, J=6.8 Hz), 3.96-4.28 (m, 4H), 1.21-1.99 (m, 30H), 0.89 (t, 3H, J=7.6 Hz).

Quelle