Reacción #75325

Ecuación de reacción

cyclohexane carboxylic acid chloride

L-alanyl-L-proline ethylamide hydrobromide

sodium hydroxide

→

N-cyclohexylcarbonyl-L-alanyl-L-proline ethylamide

Rendimiento 60.0%

Disolventes

dichloromethane

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe organic layer was separated
2. 2
   Lavadowashed with 60 ml of brine
3. 3
   Secadodried over magnesium sulphate
4. 4
   Otroevaporated
5. 5
   Otroto give a solid
6. 6
   OtroRecrystallisation from ethyl acetate

Procedimiento

1.25 g (0.00425 mol) of L-alanyl-L-proline ethylamide hydrobromide were suspended in 20 ml of dichloromethane and to the suspension were added 17.84 ml (0.00892 mol) of 0.5-N sodium hydroxide solution followed by 0.62 ml (1.1 equivalents) of cyclohexane carboxylic acid chloride. The mixture was stirred vigorously for 1 hour. The solution was diluted with 80 ml of dichloromethane, the organic layer was separated, washed with 60 ml of brine, dried over magnesium sulphate and evaporated to give a solid. Recrystallisation from ethyl acetate yielded 0.83 g (60%) of N-cyclohexylcarbonyl-L-alanyl-L-proline ethylamide of melting point 190.5°-191.5° C.; [α]D20 =-116.0° (c=1.055% in methanol).

Fuente