3-Decyldihydro-2,5-furandione → HCID 131734192, compound

HRID 1496664Notes

Reaction equation

HRID 1496664 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[C@H:5]([CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:12](=[O:24])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[NH2:6])[CH3:2].[CH2:26]([CH:36]1[CH2:41][C:40](=[O:42])[O:39][C:37]1=[O:38])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]>ClCCl>[CH2:1]([O:3][C:4](=[O:25])[C@H:5]([CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:12](=[O:24])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[NH:6][C:40](=[O:42])[CH2:41][CH:36]([C:37]([OH:39])=[O:38])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH3:2]

Participants

4

Reactant 2

HCID 867433-Decyldihydro-2,5-furandioneHCID 18395027HCID 18395027, compound

Product 1

HCID 131734192HCID 131734192, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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%.

Workup

  1. temperatureThe obtained white turbid solution was heated
  2. temperaturecooled in a freezer
  3. customto give crystals
  4. filtrationThe mixture was filtered
  5. customdried
  6. customrecrystallized

Sources & evidence

ORD record
ord-e9383888ac65474884d3b8d93eb95da7
Source dataset
uspto-grants-2015_12
Patent number
US09198846B2

Reaction notes

Loading…