Reaktion #11959

Reaktionsgleichung

compound

4-(N-Cbz aminomethyl)benzoic acid

WSCI hydrochloride

compound

Nδ-Boc-L-ornithine

→

hydrochloride

title compound

Ausbeute 38.0%

Nα-(4-(N-Cbz)aminomethylbenzoyl)-L-ornithine

Ausbeute 38.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAfter the reaction
2. 2
   Sonstigethe solvent was removed by distillation
3. 3
   workup.DISSOLUTIONThe residue was dissolved in chloroform
4. 4
   Waschenwashed with 1 mol/l aqueous solution of hydrochloric acid and saturated aqueous solution of sodium hydrogencarbonate
5. 5
   Trocknendried over sodium hydrogensulfate
6. 6
   SonstigeThe solvent was removed by distillation
7. 7
   Sonstigethe residue was purified by silica gel column chromatography (20 g, chloroform/methanol=10/1)
8. 8
   workup.DISSOLUTION130 mg of the obtained product was dissolved in methanol (2.6 ml)
9. 9
   workup.ADDITION4 mol/l hydrochloric acid/dioxane solution (2.6 ml) was added
10. 10
    SonstigeAfter the reaction
11. 11
    Sonstigethe solvent was removed by distillation
12. 12
    Sonstigethe residue was dried under vacuum

Vorschrift

The compound obtained in Example 23-2 (350 mg) was dissolved in DMF (7 ml). After the addition of WSCI hydrochloride (265.0 g), DMAP (169 mg), and the compound obtained in Example 41-1 (276.0 mg), the mixture was stirred for 24 hours at room temperature. After the reaction, the solvent was removed by distillation. The residue was dissolved in chloroform, washed with 1 mol/l aqueous solution of hydrochloric acid and saturated aqueous solution of sodium hydrogencarbonate, and dried over sodium hydrogensulfate. The solvent was removed by distillation and the residue was purified by silica gel column chromatography (20 g, chloroform/methanol=10/1). 130 mg of the obtained product was dissolved in methanol (2.6 ml) and 4 mol/l hydrochloric acid/dioxane solution (2.6 ml) was added. The mixture was stirred for 70 minutes at room temperature. After the reaction, the solvent was removed by distillation and the residue was dried under vacuum to obtain hydrochloride of the title compound (147 mg) as a white solid.

Quelle