Acetic Acid → HCID 178443296, compound

HRID 1632711Notes

Reaction equation

HRID 1632711 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].[OH-].[Na+].[C:15](Cl)(=[O:27])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].[C:29]([OH:32])(=O)[CH3:30]>O.CC(C)=O>[C:15]([N:1]([C:29](=[O:32])[CH2:30][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:8])[NH2:9])(=[O:27])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8166Dodecanoyl chloride2×HCID 14798Sodium Hydroxide2×HCID 178418600HCID 178418600, compound

Product 1

HCID 178443296HCID 178443296, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Procedure

Two grams (0.01148 mole) of L-(+) arginine were dissolved in a solution of 30 ml of water and 20 ml of acetone. To this solution were added, at room temperature, 10 ml of a 5M sodium hydroxide solution, followed immediately by the addition of one-half of a solution prepared by dissolving 5.02 gram (0.02296 mole) of lauroyl chloride in 10 ml of acetone. Fifteen minutes later, identical portions of the sodium hydroxide and lauroyl chloride solutions were added. The reaction mixture was allowed to stir overnight. The pH of the reaction mixture was then adjusted to 6 with glacial acetic acid which resulted in the precipitation of a white solid. The solid was collected by filtration and was washed with water. The washed solid then was air-dried and recrystallized from chloroform-acetone. The yield of Nα,NG -dilauroylarginine having the formula below was 0.980 gram (24.4%). ##STR4## Exactly the same procedure was used to prepare the following Nα,NG -diacyl derivatives of arginine:

Workup

  1. additionTo this solution were added, at room temperature
  2. customprepared
  3. customresulted in the precipitation of a white solid
  4. filtrationThe solid was collected by filtration
  5. washwas washed with water
  6. customThe washed solid then was air-dried
  7. customrecrystallized from chloroform-acetone
  8. customto prepare the following Nα,NG -diacyl derivatives of arginine

Sources & evidence

ORD record
ord-b72243fb0f7a4baabab55b312b9d6578
Source dataset
uspto-grants-1984_10
Patent number
US04477428

Reaction notes

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