L-Glutamine → N~2~-Dodecanoyl-L-glutamine

HRID 1858391Notes

Reaction equation

HRID 1858391 reaction equation
[C:1](Cl)(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[NH2:15][C@H:16]([C:22]([OH:24])=[O:23])[CH2:17][CH2:18][C:19](=[O:21])[NH2:20].C(N(CC)CC)C>O1CCOCC1.O>[C:1]([NH:15][C@H:16]([C:22]([OH:24])=[O:23])[CH2:17][CH2:18][C:19](=[O:21])[NH2:20])(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

6

Reactant 3

HCID 5961L-GlutamineHCID 8166Dodecanoyl chlorideHCID 8471Triethylamine

Product 1

HCID 16213882N~2~-Dodecanoyl-L-glutamine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

9.22 g lauroylchloride dissolved in 46 ml dioxane were slowly added to 6.72 g glutamine and 13.94 g triethylamin in 92 ml water and 92 ml dioxane, the temperature being 0° C. After stirring at room temperature for 1 hour, the dioxane was evaporated and the remaining solution was acidified to pH 1 with HCl. The crystals were filtered off and recrystallized from acetone and then from methanol: 9.9 g white needles.

Workup

  1. custombeing 0° C
  2. customthe dioxane was evaporated
  3. filtrationThe crystals were filtered off
  4. customrecrystallized from acetone

Sources & evidence

ORD record
ord-c60c37a1e3a54bf68eb10236bcd8afe8
Source dataset
uspto-grants-2000_11
Patent number
US06150542

Reaction notes

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