Sulfuric Acid → N~2~-Dodecanoyl-L-glutamine
Reaction equation
[NH2:1][C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5](=[O:7])[NH2:6].[OH-].[Na+].[C:13](Cl)(=[O:25])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].S(=O)(=O)(O)O>O.CC(C)=O>[C:13]([NH:1][C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5](=[O:7])[NH2:6])(=[O:25])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
108 g of L-glutamine was dissolved in 343 g of water and 102 g of aqueous 27% sodium hydroxide solution, and cooled to 10° C. 138 g of acetone was added, and 152 g of lauroyl chloride and 108 g of aqueous 27% sodium hydroxide solution were dropwise added. 300 g of the acylation liquid was diluted with water, neutralized with 35 g of 75% sulfuric acid, and filtered to obtain a white powder substance, N-lauroyl-L-glutamine. 367 g of isopropyl alcohol and 30 g of 95% sulfuric acid were added to 101.7 g of the product, and refluxed for 3.5 hours. After solvent removal, 350 g of isopropyl alcohol was added to it, and refluxed for 3 hours. After further solvent removal, 350 g of isopropyl alcohol was added and refluxed for 4 hours. The reaction liquid was left cooled to 35° C., and a white solid was collected by filtration, and dried in vacuum at 50° C. to obtain 73.14 g of a crude crystal of N-lauroyl-L-glutamine isopropyl ester (N-lauroyl-L-glutamine isopropyl ester/2-(lauroylamino)glutarimide/isopropyl N-lauroyl-2-pyrrolidone-5-carboxylate/diisopropyl N-lauryl-L-glutamate (ratio by weight)=100/16/9/16). Further, this was recrystallized from acetone to obtain 30.00 g of a pure crystal of N-lauroyl-L-glutamine isopropyl ester.
Workup
- filtrationfiltered
Sources & evidence
- ORD record
- ord-0137aaee08de4011b422ebb14216f0ad
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07850955B2
Reaction notes
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