Hydrochloric Acid → HCID 178443295, compound

HRID 488698Notes

Reaction equation

HRID 488698 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+].Cl>O.C(O)(C)C>[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 313Hydrochloric AcidHCID 8166Dodecanoyl chlorideHCID 14798Sodium Hydroxide2×HCID 178418600HCID 178418600, compound

Product 1

HCID 178443295HCID 178443295, compoundYield 92.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
11.5 °C

Procedure

To 1,106 g of L-arginine were added 6,919 g of isopropyl alcohol and 2,964 g of water. Thereto were concurrently added dropwise 1,522 g of lauroyl chloride (manufactured by Nippon Oil and Fats Co., Ltd.) and 27 wt % NaOH aqueous solution over a period of 2 hours with the pH being maintained at 10.5 to 11.5 and the reaction temperature being maintained at 10 to 13° C. After 1 hour of aging, the reaction mixture was warmed to 50° C. and adjusted to pH 3.8 by adding concentrated hydrochloric acid to dissolve the reaction product completely. Thereafter, the pH was adjusted to 6.0 by adding 27 wt % NaOH aqueous solution to precipitate crystals and the resulting slurry was gradually cooled to 10° C. with stirring. When the slurry was cooled to 10° C., the crystals were collected by filtration and washed with 10 kg of water and 4.4 kg of isopropyl alcohol, successively. The resulting washed crystals were dried under reduced pressure to obtain 2,081 g of mono-Nα-lauroyl-L-arginine as flake-shaped crystals (yield 92.3%).

Workup

  1. temperaturebeing maintained at 10.5 to 11.5
  2. temperaturethe reaction mixture was warmed to 50° C.
  3. dissolutionto dissolve the reaction product completely
  4. customto precipitate crystals
  5. temperaturethe resulting slurry was gradually cooled to 10° C.
  6. temperatureWhen the slurry was cooled to 10° C.
  7. filtrationthe crystals were collected by filtration
  8. washwashed with 10 kg of water and 4.4 kg of isopropyl alcohol
  9. washThe resulting washed crystals
  10. customwere dried under reduced pressure

Sources & evidence

ORD record
ord-2defa69e46c94773839ea6c6eb41cfca
Source dataset
uspto-grants-2005_12
Patent number
US06974582B2

Reaction notes

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