Reacción #11048

Ecuación de reacción

t-butyl pyroglutamate

tert-butyl (S)-5-oxo-2-pyrrolidinecarboxylate

Lawesson's reagent

→

title compound

Rendimiento 191.1%

tert-butyl (S)-5-thioxo-2-pyrrolidinecarboxylate

Rendimiento 191.1%

Disolventes

benzene

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaat reflux for 15.5 h
2. 2
   Concentraciónconcentrated
3. 3
   OtroThe resultant residue was purified by flash chromatography (0 to 2 to 3 to 4% MeOH/CHCl3)

Procedimiento

To a solution of t-butyl pyroglutamate (1a) (10.12 g, 54.6 mmol) in benzene (250 mL), was added Lawesson's reagent (11.05 g, 27.3 mmol). The mixture was stirred at reflux for 15.5 h, then concentrated. The resultant residue was purified by flash chromatography (0 to 2 to 3 to 4% MeOH/CHCl3) to afford 10.50 g (95%) of the title compound, 1b. 1H NMR (300 MHz, CDCl3) δ 7.27 (br s, 1H), 4.46–4.39 (m, 1H), 3.03–2.84 (m, 2H), 2.58–2.46 (m, 1H), 2.37–2.23 (m, 2H), 1.49 (s, 9H).

Fuente