Hydrochloric Acid → N-Palmitoylglycine

HRID 926808Notes

Reaction equation

HRID 926808 reaction equation
[C:1]([O:18]N1C(=O)CCC1=O)(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[NH2:26][CH2:27][C:28]([OH:30])=[O:29].C(N(CC)CC)C.Cl>CN(C=O)C.O>[NH:26]([C:1]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[O:18])[CH2:27][C:28]([OH:30])=[O:29]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 750GlycineHCID 8471TriethylamineHCID 4620598Palmitic acid N-hydroxysuccinimide2×

Product 1

HCID 151008N-PalmitoylglycineYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

A total amount (260.3 g) of N-palmitoyloxy-succinimide synthesized above was suspended in 750 ml of DMF. To the suspension, a solution of Gly (56.3 g, 0.750 mol) and triethylamine (83.2 ml, 0.598 mol) in 250 ml of water was added dropwise with stirring while cooling with ice. The whole was stirred for 30 minutes while cooled with ice, then allowed to gradually reach room temperature, and stirred for 15 hours. An aqueous solution with pH 3 that was prepared by dissolving 100 ml of 6N hydrochloric acid in 1 L of water was stirred while cooled with ice. The reaction solution containing N-palmitoyloxy-succinimide was added dropwise to the aqueous solution. The precipitated solid was collected by filtration. The precipitated solid was washed with 2 L of water and then 1 L of hexane, and recovered to give 114 g (67%) of a target compound.

Workup

  1. temperaturewhile cooling with ice
  2. stirringThe whole was stirred for 30 minutes
  3. temperaturewhile cooled with ice
  4. customallowed to gradually reach room temperature
  5. stirringstirred for 15 hours
  6. customAn aqueous solution with pH 3 that was prepared
  7. stirringwas stirred
  8. temperaturewhile cooled with ice
  9. additionwas added dropwise to the aqueous solution
  10. filtrationThe precipitated solid was collected by filtration
  11. washThe precipitated solid was washed with 2 L of water
  12. custom1 L of hexane, and recovered

Sources & evidence

ORD record
ord-3a3996a413c14d539463c0a90e814c98
Source dataset
uspto-grants-2016_03
Patent number
US09289496B2

Reaction notes

Loading…