Reaction #1583846

Reaction equation

Nε-Lauroyl-L-lysine ethyl ester

n-decyl succinic anhydride

→

Nε-lauroyl-Nα-(3-carboxytridecanoyl)-L-lysine ethyl ester

Yield 85.9%

Solvents

dichloromethane

Conditions

Workup

1. 1
   TemperatureThe obtained white turbid solution was heated
2. 2
   Temperaturecooled in a freezer
3. 3
   Otherto give crystals
4. 4
   FiltrationThe mixture was filtered
5. 5
   Otherdried
6. 6
   Otherrecrystallized

Procedure

Nε-Lauroyl-L-lysine ethyl ester (29.9 g) was dissolved in dehydrated dichloromethane (650 ml), n-decyl succinic anhydride (21.2 g) was added, and the mixture was stirred at room temperature for 24 hr. The obtained white turbid solution was heated and cooled in a freezer to give crystals. The mixture was filtered, dried, and recrystallized to give Nε-lauroyl-Nα-(3-carboxytridecanoyl)-L-lysine ethyl ester (43 g, yield 85%). 4 g thereof was dissolved in distilled ethanol (100 ml), and 4M aqueous NaOH solution (1.68 ml) was added with stirring. The mixture was stirred at room temperature for 3 hr, filtered, dried under reduced pressure, and recrystallized. yield 4.1 g, 97%.

Source