Reaktion #11944

Reaktionsgleichung

compound

Nα-(2-(N-Boc-N-2-picolylaminomethyl)pyridin-5-ylcarbonyl)-Nδ-Cbz-L-ornithine

5,6,7,8-tetrahydroquinolin-8-one

sodium cyanoborohydride

→

title compound

Ausbeute 20.5%

(2S)-2-(2-(N-Boc-N-2-picolylaminomethyl)pyridin-5-ylcarbonyl)amino-5-(5,6,7,8-tetrahydroquinolin-8-yl)aminovaleric acid

Ausbeute 20.5%

Lösungsmittel

—

solution

dioxane water

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAfter the reaction
2. 2
   Sonstigethe catalyst was removed by filtration through celite
3. 3
   Sonstigethe solvent was removed by distillation under reduced pressure
4. 4
   Sonstigeto obtain a crude product (100.2 mg)
5. 5
   workup.STIRRINGThe mixture was stirred for 22 hours at room temperature
6. 6
   SonstigeAfter the reaction
7. 7
   Sonstigethe solvent was removed by distillation
8. 8
   SonstigeThe residue was purified by silica gel column chromatography (5 g, chloroform/methanol=10/1)

Vorschrift

The compound obtained in Example 12-4 (149.9 mg) was dissolved in a dioxane/water (8/2) solution (7.5 ml). After the addition of 10% Pd—C (154.6 mg), the mixture was stirred for 4.5 hours under hydrogen atmosphere at room temperature. After the reaction, the catalyst was removed by filtration through celite and the solvent was removed by distillation under reduced pressure to obtain a crude product (100.2 mg). 75.4 mg of the crude product was dissolved in methanol (1.5 ml). Then, 5,6,7,8-tetrahydroquinolin-8-one (53.6 mg) and sodium cyanoborohydride (43.2 mg) were added. 25 drops of acetic acid was added to adjust the pH of the mixture to about 5. The mixture was stirred for 22 hours at room temperature. After the reaction, the solvent was removed by distillation. The residue was purified by silica gel column chromatography (5 g, chloroform/methanol=10/1) to obtain the title compound (30.6 mg) as white foam.

Quelle