Reaktion #5494

Reaktionsgleichung

Trans 3-(acetylthiomethyl)-2-oxo-1-azacyclodecane-10-carboxylic acid

3-aminopyridine

1-hydroxybenzotriazole

4-methylmorpholine

N-(dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride

→

3-{N-[[trans 3-(acetylthiomethyl)-2-oxo-1-azacyclodecan-10-yl]-carbonyl]-amino}-pyridine

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto warm up to room temperature
2. 2
   SonstigeThe reaction is partitioned between methylene chloride and water
3. 3
   Trocknenthe organic layer is dried (MgSO4)
4. 4
   Sonstigethe solvent is evaporated
5. 5
   SonstigeThe product is purified by silica gel chromatography (70% ethyl acetate/hexane)

Vorschrift

Trans 3-(acetylthiomethyl)-2-oxo-1-azacyclodecane-10-carboxylic acid (0.100 g, 0.35 mmol), 3-aminopyridine (0.036 g, 0.38 mmol), 1-hydroxybenzotriazole (0.047 g, 0.035 mmol), and 4-methylmorpholine (0.077 mL, 0.70 mmol) are dissolved in methylene chloride (2.5 mL), and the reaction is cooled to 0° C. To this solution is added N-(dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (0.134 g, 0.70 mmol), and the reaction is allowed to warm up to room temperature and then stirred overnight. The reaction is partitioned between methylene chloride and water, the organic layer is dried (MgSO4), and the solvent is evaporated. The product is purified by silica gel chromatography (70% ethyl acetate/hexane) to give 3-{N-[[trans 3-(acetylthiomethyl)-2-oxo-1-azacyclodecan-10-yl]-carbonyl]-amino}-pyridine, MS: M+1=364.

Quelle