Triethylamine → N-(3,7,11,15-Tetramethyl-2,6,10,14-hexadecatetraenoyl)-glycine

HRID 34561

Reaction equation

HRID 34561 reaction equation
[CH3:1][C:2]([CH2:7][CH2:8][CH:9]=[C:10]([CH3:22])[CH2:11][CH2:12][CH:13]=[C:14]([CH3:21])[CH2:15][CH2:16][CH:17]=[C:18]([CH3:20])[CH3:19])=[CH:3][C:4]([OH:6])=O.Cl.C([O:26][C:27](=[O:30])[CH2:28][NH2:29])C.C(N(CC)CC)C.[OH-].[K+]>C(O)C.O>[CH3:1][C:2]([CH2:7][CH2:8][CH:9]=[C:10]([CH3:22])[CH2:11][CH2:12][CH:13]=[C:14]([CH3:21])[CH2:15][CH2:16][CH:17]=[C:18]([CH3:20])[CH3:19])=[CH:3][C:4]([NH:29][CH2:28][C:27]([OH:30])=[O:26])=[O:6]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 14797Potassium HydroxideHCID 1285703,7,11,15-Tetramethyl-2,6,10,14-hexadecatetraenic acidHCID 2723640Glycine ethyl ester, hydrochloride

Product 1

HCID 54055783N-(3,7,11,15-Tetramethyl-2,6,10,14-hexadecatetraenoyl)-glycineYield 85%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The reaction of 6.1 g of 3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenoic acid with glycine ethyl ester hydrochloride was conducted in the same manner as described in Example 1 except that 6.5 ml of triethylamine was used. Then, a solution of 2.7 g of potassium hydroxide in ethanol was added. The mixture was heated under reflux for 30 minutes. After the completion of the reaction, water was added and the obtained aqueous solution was extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried over magnesium sulfate. The solvent was distilled off to afford 6.1 g (yield 85%) of the title compound as a pale brown oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 30 minutes
  3. additionwas added
  4. extractionthe obtained aqueous solution was extracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with water
  6. dry with materialdried over magnesium sulfate
  7. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-1d5e702110244a0e832fd0d8c9e22490
Source dataset
uspto-grants-1988_08
Patent number
US04762829

Linked notes

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