Reaktion #75325

Reaktionsgleichung

cyclohexane carboxylic acid chloride

L-alanyl-L-proline ethylamide hydrobromide

sodium hydroxide

→

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

Ausbeute 60.0%

Lösungsmittel

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe organic layer was separated
2. 2
   Waschenwashed with 60 ml of brine
3. 3
   Trocknendried over magnesium sulphate
4. 4
   Sonstigeevaporated
5. 5
   Sonstigeto give a solid
6. 6
   SonstigeRecrystallisation from ethyl acetate

Vorschrift

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).

Quelle