Reacción #1583843

Ecuación de reacción

L-(+)-glutamine

NaOH

2-ethylhexyl isocyanate

→

N2-[(2-ethylhexylamino)carbonyl]-L-glutamine

Rendimiento 88.2%

Disolventes

water dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrorose to 20° C.
2. 2
   Filtraciónfiltered
3. 3
   LavadoThe filtrate was washed twice with ethyl acetate (200 ml)
4. 4
   FiltraciónFiltration of the resulting precipitate
5. 5
   Otrodrying under vacuum

Procedimiento

At 5° C., a suspension of L-(+)-glutamine (23.1 g, 158 mmol) in 1:1 water/dioxane (300 ml) was treated successively with a solution of 2N aq. NaOH (79 ml) and with 2-ethylhexyl isocyanate (25 g, 158 mmol). The resulting mixture was stirred for 24 h while its temperature rose to 20° C. (final pH value: 6) and filtered. The filtrate was washed twice with ethyl acetate (200 ml) and the combined organic phases were acidify with a 2N aq. HCl solution to pH 1. Filtration of the resulting precipitate and drying under vacuum gave N2-[(2-ethylhexylamino)carbonyl]-L-glutamine (42 g, 88%, white solid).

Fuente