Réaction #317014

Équation de réaction

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide

furan-2-carboxylic acid

(S)-2-Amino-3-cyclohexyl-N-((3S,4S,7R)-3-hydroxy-7-methyl-1-propyl-azepan-4-yl)-propionamide

4-methylmorpholine

hydroxybenztriazole

→

title compound

Rendement 76.9%

Furan-2-carboxylic acid [(S)-2-cyclohexyl-1-((3S,4S,7R)-3-hydroxy-7-methyl-1-propyl-azepan-4-ylcarbamoyl)-ethyl]-amide

Rendement 76.9%

Solvants

EtOAc

DMF

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction mixture was then warmed to RT
2. 2
   workup.STIRRINGwas stirred overnight
3. 3
   Lavagewashed with H2O, brine
4. 4
   Séchagedried with magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated in vacuo by rotary evaporation
7. 7
   Autrechromatographed (silica gel, 2.5% MeOH/CH2Cl2)

Mode opératoire

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide (0.10 g, 0.53 mmol) was added to a solution of furan-2-carboxylic acid (0.059 g, 0.53 mmol), (S)-2-Amino-3-cyclohexyl-N-((3S,4S,7R)-3-hydroxy-7-methyl-1-propyl-azepan-4-yl)-propionamide (0.15 g, 0.36 mmol), 4-methylmorpholine (0.14 g, 0.16 ml, 1.44 mmol), hydroxybenztriazole (0.071 g, 0.53 mmol) in DMF (2.0 ml) and was stirred at RT overnight. The reaction mixture was then warmed to RT and was stirred overnight. The reaction mixture was diluted with EtOAc (30 ml), washed with H2O, brine, dried with magnesium sulfate, filtered, concentrated in vacuo by rotary evaporation, and chromatographed (silica gel, 2.5% MeOH/CH2Cl2) to yield the title compound (0.12 g, 76%): Electrospray mass spec: M+H+=434.2.

Source