Reaction #5494

Reaction equation

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

Solvents

methylene chloride

Conditions

Workup

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

Procedure

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.

Source