反応 #11944

反応方程式

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

収率 20.5%

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

収率 20.5%

溶媒

—

solution

dioxane water

methanol

反応条件

後処理

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

実験手順

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.

出典