Hydrochloric Acid → HCID 131734193, compound

HRID 1496665Notes

Reaction equation

HRID 1496665 reaction equation
[C:1]([NH:14][CH2:15][CH2:16][CH2:17][CH2:18][C@@H:19]([C:21]([OH:23])=[O:22])[NH2:20])(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].CC[O:26][CH2:27][CH3:28].Cl>[OH-].[Na+]>[C:1]([NH:14][CH2:15][CH2:16][CH2:17][CH2:18][C@@H:19]([C:21]([OH:23])=[O:22])[NH:20][C:27](=[O:26])[CH2:28][CH2:17][CH2:18][CH2:19][C:21]([OH:23])=[O:22])(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether2×HCID 104151L-Lysine, N6-(1-oxododecyl)-

Product 1

HCID 131734193HCID 131734193, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

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%.

Workup

  1. stirringwith stirring
  2. filtrationThe precipitated crystals were filtered
  3. customrecrystallized

Sources & evidence

ORD record
ord-7878d13113e443cd9f33911ff8643462
Source dataset
uspto-grants-2015_12
Patent number
US09198846B2

Reaction notes

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