Reaction #1583847

Reaction equation

Nε-Lauroyl-L-lysine

ether

ether

hydrochloric acid

→

Nε-lauroyl-Nα-(5-carboxypentanoyl)-L-lysine

Yield 66.0%

Solvents

NaOH

Conditions

Workup

1. 1
   workup.STIRRINGwith stirring
2. 2
   FiltrationThe precipitated crystals were filtered
3. 3
   Otherrecrystallized

Procedure

Nε-Lauroyl-L-lysine (30 g) was dissolved in 0.2M aqueous NaOH solution (1 L), and ether was added. Adipic acid monoethyl ester acid chloride (26.4 g) was added to the ether layer, and the mixture was stirred at room temperature for 24 hr. To the aqueous solution was added hydrochloric acid with stirring, and the mixture was adjusted to about pH 1. The precipitated crystals were filtered and recrystallized to give Nε-lauroyl-Nα-(5-carboxypentanoyl)-L-lysine (27.42 g, yield 66%). 4.566 g thereof was dissolved in methanol (50 ml), 1M aqueous NaOH solution (10 ml) was added, and the mixture was stirred at room temperature for 3 hr. The solution was filtered, the solvent was removed, and the obtained solid was recrystallized. yield 4.7 g, 99%.

Source