Palmitoyl chloride → Palmitic acid N-hydroxysuccinimide

HRID 926807Notes

Reaction equation

HRID 926807 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8].[C:9](Cl)(=[O:25])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].C(N(CC)CC)C>C(Cl)(Cl)Cl>[C:9]([O:1][N:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8])(=[O:25])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 8206Palmitoyl chlorideHCID 8471TriethylamineHCID 80170N-Hydroxysuccinimide

Product 1

HCID 4620598Palmitic acid N-hydroxysuccinimide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

N-hydroxysuccinimide (69.8 g, 0.598 mol) was added drop by drop to 1 L of chloroform solution of palmitoyl chloride (165 ml, 0.544 mol) with stirring while cooling with ice, and then triethylamine (83.1 ml, 0.598 mol) was added dropwise over 30 minutes. Then, the whole was stirred while cooled with ice for 30 minutes, allowed to gradually reach room temperature, and stirred for 7 hours. The reaction mixture was washed with water (500 ml×3), then dried over magnesium sulfate, and concentrated under reduced pressure to give 260.3 g (quant) of a colorless solid.

Workup

  1. temperaturewhile cooling with ice
  2. stirringThen, the whole was stirred
  3. temperaturewhile cooled with ice for 30 minutes
  4. customallowed to gradually reach room temperature
  5. stirringstirred for 7 hours
  6. washThe reaction mixture was washed with water (500 ml×3)
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customto give 260.3 g (quant) of a colorless solid

Sources & evidence

ORD record
ord-25431a3709e941349a72711ab27a632d
Source dataset
uspto-grants-2016_03
Patent number
US09289496B2

Reaction notes

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