Hydrochloric Acid → N-alpha-undec-10-enoyl-glutamic acid

HRID 1668837Notes

Reaction equation

HRID 1668837 reaction equation
[NH2:1][C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5](=[O:7])N.[OH-:11].[K+].[C:13](Cl)(=[O:24])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH:22]=[CH2:23].Cl>O.C1COCC1>[C:13]([NH:1][C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5]([OH:11])=[O:7])(=[O:24])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH:22]=[CH2:23]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5961L-GlutamineHCID 14797Potassium HydroxideHCID 3804210-Undecenoyl chloride

Product 1

HCID 57102536N-alpha-undec-10-enoyl-glutamic acidYield 30%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

L-Glutamine (14.62 g, 0.1 mol) and KOH (11.2 g, 0.2 mol) were dissolved in water (200 mL) at 20° C. A solution of 10-undecenoyl chloride (20.3 g, 0.1 mol) in THF (200 mL) was then added over 10 minutes. The reaction was stirred for 16 hours at 20° C. and was then reduced in vacuo to a volume of approximately 250 mL. Concentrated HCl (circa 12M) was added dropwise until the solution was pH 1. The white solid precipitate was collected by filtration. This solid was washed with water (100 mL) and diethyl ether (100 mL). The solid was then dissolved in refluxing toluene (500 mL) and the excess water present was removed by distillation at ambient pressure using a Dean-Stark trap. The solution was then allowed to cool to 20° C. After 16 hours, the white solid precipitate was collected via filtration and recrystallized from EtOAc (500 mL). This solid was dried in vacuo to give N-α-undec-10-enoyl-glutamic acid (9.36 g, 30%) as a white powder.

Workup

  1. filtrationThe white solid precipitate was collected by filtration
  2. washThis solid was washed with water (100 mL) and diethyl ether (100 mL)
  3. dissolutionThe solid was then dissolved
  4. temperaturein refluxing toluene (500 mL)
  5. customthe excess water present was removed by distillation at ambient pressure
  6. temperatureto cool to 20° C
  7. waitAfter 16 hours
  8. filtrationthe white solid precipitate was collected via filtration
  9. customrecrystallized from EtOAc (500 mL)
  10. customThis solid was dried in vacuo

Sources & evidence

ORD record
ord-75af5b8aa45441e6a0e9a54904988157
Source dataset
uspto-grants-2011_08
Patent number
US07989466B2

Reaction notes

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