Reacción #1253202

Ecuación de reacción

L-arginine

sulfuric acid

dodecanol

→

arginine dodecyl ester

Rendimiento 86.0%

Disolventes

diethyl ether

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroa clear light yellow solution resulted
2. 2
   Otrothe reaction
3. 3
   Lavadowashed with water (3×25 ml)
4. 4
   LavadoThe combined aqueous extracts were washed with diethyl ether (2×25 ml)
5. 5
   Otroprecipitated
6. 6
   FiltraciónFiltration of the suspension
7. 7
   Lavadowashing of the filtrate with water (3× with 25 ml), acetone (3× with 25 ml) and diethyl ether (3× with 25 ml)

Procedimiento

A suspension of L-arginine free base (0.6 g, 3.5 mmol), sulfuric acid (0.31 ml, 7 mmol), and dodecanol (25 ml) were stirred together at 140° C. under nitrogen. After 6 hours, a clear light yellow solution resulted, and TLC indicated the reaction to be complete. The reaction mixture was diluted with diethyl ether (50 ml), and washed with water (3×25 ml). The combined aqueous extracts were washed with diethyl ether (2×25 ml), and basified with 1N KOH solution, upon which a white solid precipitated. Filtration of the suspension and washing of the filtrate with water (3× with 25 ml), acetone (3× with 25 ml) and diethyl ether (3× with 25 ml) gave arginine dodecyl ester. The yield was 86%. Melting point was 125-130° C. NMR gave the expected results for arginine dodecyl ester.

Fuente