Reaktion #966416

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-benzotriazol 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-oxoheptane-4-yl]-N-methyl-L-valinamide

Lösungsmittel

ethyl acetate

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe organic phase was separated off
2. 2
   Waschenwashed successively with saturated sodium hydrogen carbonate solution and saturated sodium chloride solution
3. 3
   Trocknendried over magnesium sulphate
4. 4
   Filtrationfiltered
5. 5
   Sonstigeevaporated
6. 6
   SonstigeThe residue was used directly in the next step, without purification

Vorschrift

396 mg (1.1 mmol) N-[(9H-fluoren-9-ylmethoxy)carbonyl]-N-methyl-L-valine were dissolved in 20 ml DMF and 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-benzotriazol hydrate were added in succession. The mixture was stirred overnight at RT. The mixture was then poured into a solution of semi-saturated aqueous ammonium chloride and ethyl acetate. The organic phase was separated off, washed successively with saturated sodium hydrogen carbonate solution and saturated sodium chloride solution, then dried over magnesium sulphate, filtered and evaporated. The residue was used directly in the next step, without purification.

Quelle