Reaktion #660186

Reaktionsgleichung

tert-butyl-(3R,4S,5S)-3-methoxy-5-methyl-4-[methyl(L-valyl)amino]heptanoate

intermediate 2

tert-butyl-(3R,4S,5S)-3-methoxy-5-methyl-4-[methyl(L-valyl)amino]heptanoate

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

1-hydroxy-1H-benzotriazole hydrate

ammonium chloride

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-N-methyl-L-valine

→

N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-N-methyl-L-valyl-N-[(3R,4S,5S)-1-tert-butoxy-3-methoxy-5-methyl-1-oxoheptan-4-yl]-N-methyl-L-valinamide

Lösungsmittel

ethyl acetate

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe organic phase was separated
2. 2
   Waschenwashed in succession with saturated sodium bicarbonate solution and saturated sodium chloride solution
3. 3
   Trocknendried over magnesium sulfate
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated
6. 6
   SonstigeThe residue was used directly in the next step without further purification

Vorschrift

396 mg (1.1 mmol) N-[(9H-fluoren-9-ylmethoxy)carbonyl]-N-methyl-L-valine was dissolved in DMF and then mixed in succession with 365 mg (1 mmol) tert-butyl-(3R,4S,5S)-3-methoxy-5-methyl-4-[methyl(L-valyl)amino]heptanoate (intermediate 2), 234 mg (1.2 mmol) 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 187 mg (1.2 mmol) 1-hydroxy-1H-benzotriazole hydrate. The mixture was stirred over night at RT. The batch was then poured into a mixture of 50% saturated aqueous ammonium chloride solution and ethyl acetate. The organic phase was separated, washed in succession with saturated sodium bicarbonate solution and saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated. The residue was used directly in the next step without further purification.

Quelle