Sulfuric Acid → HCID 178443295, compound

HRID 488701Notes

Reaction equation

HRID 488701 reaction equation
[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:9])[NH2:8].[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].[OH-].[Na+].S(=O)(=O)(O)O>O.CC(C)=O>[C:13]([NH:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:8])[NH2:9])(=[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

7

Reactant 4

HCID 1118Sulfuric AcidHCID 8166Dodecanoyl chlorideHCID 14798Sodium HydroxideHCID 178418600HCID 178418600, compound

Product 1

HCID 178443295HCID 178443295, compoundYield 85.7%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

To 35.0 g of L-arginine were added 118.7 g of acetone and 200 g of water. Thereto were concurrently added dropwise 36.5 g of lauroyl chloride (“lauroyl chloride” manufactured by Nippon Oil and Fats Co., Ltd.) and 45 ml of 8N NaOH aqueous solution over a period of 2 hours with the pH being maintained at 11.5 to 12.0 and the reaction temperature being maintained at 15 to 25° C. After 2 hours of aging, the reaction mixture was adjusted to pH 5.0 with 6N sulfuric acid with cooling and then poured into about 300 ml of ice-water to precipitate crude crystals of mono-Nα-lauroyl-L-arginine, which were collected by filtration and then dried (yield 55 g). The crude crystals were washed by stirring in 300 ml of petroleum benzine and then filtered, and the crystals were dried under reduced pressure to obtain 51 g of mono-Nα-lauroyl-L-arginine (yield 85%).

Workup

  1. temperaturebeing maintained at 11.5 to 12.0
  2. temperaturewith cooling
  3. customto precipitate crude crystals of mono-Nα-lauroyl-L-arginine, which
  4. filtrationwere collected by filtration
  5. customdried (yield 55 g)
  6. washThe crude crystals were washed
  7. filtrationfiltered
  8. customthe crystals were dried under reduced pressure

Sources & evidence

ORD record
ord-ba2065657a0247ca9f72de749e89bd63
Source dataset
uspto-grants-2005_12
Patent number
US06974582B2

Reaction notes

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