Réaction #55626

Équation de réaction

N-benzyloxycarbonyloxysuccinimide

water

γ-aminobutyric acid

sodium bicarbonate

→

N-carbobenzoxy-γ-aminobutyric acid

Solvants

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   Autrethe tetrahydrofuran is evaporated in vacuo
2. 2
   workup.ADDITIONThe residue is diluted with 200 ml
3. 3
   Extractionof water and extracted with (2×300 ml.) anhydrous ether
4. 4
   Extractionextracted with (3×400 ml.) methylene chloride
5. 5
   AutreThe methylene chloride extracts are collected
6. 6
   Lavagewashed with (3×200 ml.) brine solution
7. 7
   Séchagedried with anhydrous magnesium sulfate
8. 8
   Autrethe solvent evaporated in vacuo at room temperature

Mode opératoire

To a solution of 100 ml. of water and 120 ml. of tetrahydrofuran is added sequentially 12.4 g. of γ-aminobutyric acid, 10.4 g. of sodium bicarbonate, and 30 g. of N-benzyloxycarbonyloxysuccinimide. The reaction mixture is stirred for approximately 3.5 hours at room temperature and then the tetrahydrofuran is evaporated in vacuo. The residue is diluted with 200 ml. of water and extracted with (2×300 ml.) anhydrous ether. The aqueous layer is then acidified to pH 1-2 with 1 N hydrochloric acid and extracted with (3×400 ml.) methylene chloride. The methylene chloride extracts are collected and combined and then washed with (3×200 ml.) brine solution, dried with anhydrous magnesium sulfate and the solvent evaporated in vacuo at room temperature. The residue provides N-carbobenzoxy-γ-aminobutyric acid.

Source