Reacción #2870

Ecuación de reacción

Imidazole

t-butyldimethylchlorosilane

5-pyridin-3-yl-thiophene-2-sulfonic acid {1-[5-cyano-2-hydroxy-benzyl]-2-oxo-pyrrolidin-3-yl}-amide

→

oil

Rendimiento 74.5%

5-Pyridin-3-yl-thiophene-2-sulfonic acid {1-[2-(tert-butyl-dimethyl-silanyloxy)-5-cyano-benzyl]-2-oxo-pyrrolidin-3-(S)-yl}amide

Rendimiento 74.5%

Disolventes

DMF

EtOAc

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowashed with saturated NaHCO3 (aq) and brine
2. 2
   SecadoThe organic layer is dried over MgSO4
3. 3
   Filtraciónfiltered
4. 4
   Concentraciónconcentrated
5. 5
   OtroThe product is purified by column chromatography
6. 6
   Lavadoeluting with 3% MeOH/CH2Cl2

Procedimiento

Imidazole (0.094 g, 1.37 mmol) and t-butyldimethylchlorosilane (0.099 g, 0.66 mmol) are added to a solution of 5-pyridin-3-yl-thiophene-2-sulfonic acid {1-[5-cyano-2-hydroxy-benzyl]-2-oxo-pyrrolidin-3-yl}-amide (0.25 g, 0.55 mmol) in 10 mL of DMF. The resulting mixture is stirred overnight, then diluted with EtOAc and washed with saturated NaHCO3 (aq) and brine. The organic layer is dried over MgSO4, filtered and concentrated. The product is purified by column chromatography eluting with 3% MeOH/CH2Cl2 to give a brown oil (0.236 g, 0.41 mmol).

Fuente