Reaktion #11961

Reaktionsgleichung

compound

(S)-2-((4-aminomethylbenzoyl)amino)-5-(N-Boc-2-picolylaminomethyl)valeric acid

nitrate

triethylamine

→

title compound

(S)-2-((4-guanidinomethylbenzoyl)amino)-5-(2-picolylaminomethyl)valeric acid

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe reaction solution was concentrated
2. 2
   workup.ADDITIONChloroform was added to the residue
3. 3
   Waschenthe mixture was washed with saturated aqueous solution of sodium hydrogencarbonate
4. 4
   EinengenThe organic layer was concentrated
5. 5
   Sonstigedried under reduced pressure
6. 6
   SonstigeThe residue was purified by silica gel column chromatography (5 g, chloroform/methanol/water=7/3/0.5)

Vorschrift

The compound obtained in Example 41-5 (0.01 g) was dissolved in DMF (0.3 ml). After the addition of dimethylpyrazolecarboxyamidine nitrate (0.01 g), the mixture was adjusted to pH 8 with triethylamine and stirred for 3 days. The reaction solution was concentrated. Chloroform was added to the residue and the mixture was washed with saturated aqueous solution of sodium hydrogencarbonate. The organic layer was concentrated and dried under reduced pressure. The residue was purified by silica gel column chromatography (5 g, chloroform/methanol/water=7/3/0.5) to obtain the title compound (0.01 g) as white foam. The foam was dissolved in methanol (0.3 ml) and 4 mol/l hydrochloric acid/dioxane solution (0.3 ml) was added dropwise. The mixture was stirred for 3 hours at room temperature. The reaction solution was concentrated and dried under reduced pressure to obtain a crude product (0.01 g). The crude product was purified by silica gel column chromatography (0.5 g, chloroform/methanol/water=7/3/0.5) and 1 mol/l hydrochloric acid was added. The mixture was concentrated to obtain hydrochloride of the title compound (0.01 g) as white foam.

Quelle