Reacción #75322

Ecuación de reacción

L-alanyl-L-proline ethylamide hydrobromide

pivaloyl chloride

→

N-pivaloyl-L-alanyl-L-proline ethylamide

Rendimiento 40.0%

Disolventes

pyridine

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe pyridine was removed by evaporation
2. 2
   OtroThe oil was triturated with toluene
3. 3
   Otrore-evaporated
4. 4
   Otropartitioned between chloroform and saturated brine
5. 5
   OtroThe chloroform layer was separated
6. 6
   Secadodried over magnesium sulphate
7. 7
   Filtraciónfiltered off
8. 8
   Otroevaporated to a clear oil which
9. 9
   Otrocrystallised on the addition of petrol
10. 10
    FiltraciónThe solid was filtered off
11. 11
    Lavadowashed with petrol
12. 12
    Otrodried

Procedimiento

1 g (0.0033 mol) of L-alanyl-L-proline ethylamide hydrobromide was dissolved in 20 ml of dry pyridine and 0.45 ml of pivaloyl chloride was added. The mixture was stirred for 1 hour at room temperature and then the pyridine was removed by evaporation. The oil was triturated with toluene, re-evaporated and then partitioned between chloroform and saturated brine. The chloroform layer was separated and dried over magnesium sulphate, filtered off and evaporated to a clear oil which crystallised on the addition of petrol. The solid was filtered off, washed with petrol and dried to yield 0.4 g (40%) of N-pivaloyl-L-alanyl-L-proline ethylamide of melting point 94°-96° C.

Fuente