Reacción #75324

Ecuación de reacción

L-alanyl-L-proline ethylamide hydrobromide

N-ethylmorpholine

ethyl chloroformate

→

N-ethoxycarbonyl-L-alanyl-L-proline ethylamide

Rendimiento 47.0%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe solvent was evaporated off
2. 2
   workup.DISSOLUTIONthe residue dissolved in 100 ml of chloroform
3. 3
   Lavadowashed successively with 2-N hydrochloric acid in brine, brine, saturated sodium bicarbonate solution and brine
4. 4
   Secadodried over magnesium sulphate
5. 5
   Otroevaporated to an oil which
6. 6
   Otrosoon crystallised
7. 7
   OtroRecrystallisation from chloroform/petrol

Procedimiento

2 g (0.0066 mol) of L-alanyl-L-proline ethylamide hydrobromide were suspended in 20 ml of dry tetrahydrofuran, 1.84 ml (0.0145 mol) of N-ethylmorpholine and 0.76 ml (0.0079 mol) of ethyl chloroformate were added and the mixture was stirred at room temperature for 2 hours. The solvent was evaporated off and the residue dissolved in 100 ml of chloroform and washed successively with 2-N hydrochloric acid in brine, brine, saturated sodium bicarbonate solution and brine, dried over magnesium sulphate and evaporated to an oil which soon crystallised. Recrystallisation from chloroform/petrol yielded 0.88 g (47%) of N-ethoxycarbonyl-L-alanyl-L-proline ethylamide of melting point 126°-128° C.; [α]D20 =-117.6° (c=1.02% in methanol).

Fuente