반응 #5496

반응 방정식

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

1-acetoxy-2-aminoethane hydrochloride

1-hydroxybenzotriazole

4-methylmorpholine

N-(dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride

→

2-acetoxy-N-[[trans 3-(acetylthiomethyl)-2-oxo-1-azacyclodecan-10-yl]-carbonyl]-ethylamine

용매

methylene chloride

methylene chloride

반응 조건

후처리

1. 1
   온도to warm up to room temperature
2. 2
   세척the organic layer is washed with 1N hydrochloric acid, saturated sodium bicarbonate
3. 3
   건조dried (MgSO4)
4. 4
   기타the solvent is evaporated
5. 5
   기타The product is purified by silica gel chromatography (75% ethyl acetate/hexane)

실험 절차

Trans 3-(acetylthiomethyl)-2-oxo-1-azacyclodecane-10-carboxylic acid (0.15 g, 0.52 mmol), 1-acetoxy-2-aminoethane hydrochloride (0.073 g, 0.52 mmol), 1-hydroxybenzotriazole (0.12 g, 0.52 mmol), and 4-methylmorpholine (0.17 mL, 1.56 mmol) are dissolved in methylene chloride (3.0 mL), and the reaction is cooled to 0° C. To this solution is added N-(dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (0.20 g, 1.04 mmol), and the reaction is allowed to warm up to room temperature and then stirred overnight. The reaction is diluted with more methylene chloride, and the organic layer is washed with 1N hydrochloric acid, saturated sodium bicarbonate, dried (MgSO4), and the solvent is evaporated. The product is purified by silica gel chromatography (75% ethyl acetate/hexane) to give 2-acetoxy-N-[[trans 3-(acetylthiomethyl)-2-oxo-1-azacyclodecan-10-yl]-carbonyl]-ethylamine, MS: M+1=373.

출처