Réaction #1552038

Équation de réaction

hydrochloric acid

N-palmitoyloxy-succinimide

Gly

triethylamine

→

desired compound

Rendement 67.0%

N-palmitoyl-Gly

Rendement 67.0%

Solvants

water

water

DMF

Conditions de réaction

Traitement

1. 1
   Températurewhile cooled with ice
2. 2
   workup.ADDITIONwere added dropwise
3. 3
   AutreTo an aqueous solution obtained
4. 4
   Températurewhile cooled with ice
5. 5
   workup.STIRRINGwith stirring
6. 6
   workup.ADDITIONthe reaction solution was added dropwise
7. 7
   Autreto precipitate a solid, which
8. 8
   Filtrationwas filtered off
9. 9
   LavageThe resultant product was washed with 2 L of water
10. 10
    Autrewith 1 L of hexane, and was then collected

Mode opératoire

260.3 g of the N-palmitoyloxy-succinimide synthesized above as a whole was suspended in 750 ml of DMF and, to the resultant solution while cooled with ice with stirring, 56.3 g (0.750 mol) of Gly and 83.2 mL (0.598 mol) of triethylamine dissolved in 250 ml of water were added dropwise. The resultant solution was stirred for another 30 minutes while cooled with ice and for another 15 hours during which the resultant solution gradually reached room temperature. To an aqueous solution obtained by dissolving 100 mL of 6 N hydrochloric acid in 1 L of water and adjusting the pH to pH 3, while cooled with ice with stirring, the reaction solution was added dropwise to precipitate a solid, which was filtered off. The resultant product was washed with 2 L of water and then with 1 L of hexane, and was then collected to obtain 114 g (67%) of a desired compound.

Source