反应 #1435765

反应方程式

hydrochloric acid

(S)-7-amino-9-methyl-6,7-dihydro-9H-5-oxa-9-aza-benzocyclohepten-8-one

N-(2,2,3,3,3-pentafluoro-propyl)-malonamic acid

1-hydroxybenzotriazole hydrate

N-(3-dimethylaminopropyl)-N′-ethyl-carbodiimid-hydrochloride

diisopropylethylamine

→

N-((S)-9-methyl-8-oxo-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl)-N′-(2,2,3,3,3-pentafluoro-propyl)-malonamide

收率 39.4%

溶剂

tetrahydrofurane

反应条件

后处理

1. 1
   萃取Extraction with dichloromethane
2. 2
   洗涤by washing with saturated aqueous sodium bicarbonate solution
3. 3
   干燥drying with sodium sulfate, and chromatography on silicagel with ethylacetate/heptane

实验过程

To a solution of 0.06 g (0.31 mmol) (S)-7-amino-9-methyl-6,7-dihydro-9H-5-oxa-9-aza-benzocyclohepten-8-one in 5 ml tetrahydrofurane were added 0.07 g (0.31 mmol) N-(2,2,3,3,3-pentafluoro-propyl)-malonamic acid, 0.04 g (0.31 mmol) 1-hydroxybenzotriazole hydrate, 0.06 g (0.31 mmol) N-(3-dimethylaminopropyl)-N′-ethyl-carbodiimid-hydrochloride and 0.1 ml (0.62 mmol) diisopropylethylamine. After stirring at room temperature over night the mixture was added to 1N aqueous hydrochloric acid. Extraction with dichloromethane, followed by washing with saturated aqueous sodium bicarbonate solution and drying with sodium sulfate, and chromatography on silicagel with ethylacetate/heptane yielded 0.05 g (39%) N-((S)-9-methyl-8-oxo-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-yl)-N′-(2,2,3,3,3-pentafluoro-propyl)-malonamide as white solid, MS m/e (%): 410.3 (M+H+, 100).

来源