Reacción #350102

Ecuación de reacción

pyridine

4-(n-hexadecylamino)benzoic acid

dioxane

t-butylazidoformate

→

title compound

N-(t-butyloxycarbonyl)-4-(n-hexadecylamino)benzoyl-imidazole

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe protected amido-acid is precipitated from solution by addition of 150 ml, of water
2. 2
   OtroThe product is collected
3. 3
   Otrothoroughly dried
4. 4
   workup.DISSOLUTIONThe crude product is dissolved in 200 ml
5. 5
   workup.ADDITIONto this is added 5.4 g
6. 6
   workup.STIRRINGThe solution is stirred overnight at room temperature
7. 7
   Otrothe solvents are evaporated

Procedimiento

A solution of 10 g. of 4-(n-hexadecylamino)benzoic acid in 100 ml. dioxane is treated with 4.0 g. of t-butylazidoformate and 10 ml. pyridine. After stirring at room temperature for 18 hours, the protected amido-acid is precipitated from solution by addition of 150 ml, of water. The product is collected and thoroughly dried. The crude product is dissolved in 200 ml. of a mixture consisting of methylene chloride/dimethoxy ethane/pyridine (1:4:1), and to this is added 5.4 g. of 1,1'-carbonyldimidazole. The solution is stirred overnight at room temperature and the solvents are evaporated to yield the title compound as a thick, orange oil.

Fuente