Reacción #83139

Ecuación de reacción

α-trimethylsilylethoxymethyl-DL-tryptophan methyl ester

diisopropylethylamine

2-adamantylchloroformate

→

title compound

Rendimiento 67.8%

N-[(2-Adamantyloxy)carbonyl]-α-trimethylsilylethoxymethyl-DL-tryptophan methyl ester

Rendimiento 67.8%

Disolventes

THF

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted with ethyl acetate (4×50 mL)
2. 2
   ExtracciónThe organic extract
3. 3
   Lavadowas washed with brine
4. 4
   Secadodried over Na2SO4
5. 5
   OtroEvaporation of the organic solvent

Procedimiento

A mixture of α-trimethylsilylethoxymethyl-DL-tryptophan methyl ester (1.0 g, 2.8 mmol), diisopropylethylamine (0.4 g, 3 mmol) and 2-adamantylchloroformate (0.65 g, 3 mmol) in 20 mL dry THF was stirred at room temperature for 4 hours. The reaction mixture was diluted with distilled water and extracted with ethyl acetate (4×50 mL). The organic extract was washed with brine and dried over Na2SO4. Evaporation of the organic solvent gave the title compound as a colorless foam (1.0 g, 67.8%).

Fuente