Reaktion #2206206

Reaktionsgleichung

Trans-4-guanidinomethylcyclohexanecarboxylic acid hydrochloride

dicyclohexylcarbodiimide

benzyl anthranilate

pyridine

→

N-(o-benzyloxycarbonylphenyl)-trans-4-guanidinomethylcyclohexanecarboxamide hydrochloride

Ausbeute 55.3%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONis added to the reaction mixture
2. 2
   workup.STIRRINGthe mixture is stirred for 30 minutes
3. 3
   Filtrationthe undissolved materials are filtered off
4. 4
   EinengenThe filtrate is concentrated to driness
5. 5
   WaschenThe resulting residue is washed with ethyl acetate (100 ml)
6. 6
   Sonstigerecrystallized from water

Vorschrift

Trans-4-guanidinomethylcyclohexanecarboxylic acid hydrochloride (3.0 g, 0.013 mole) (which is prepared by the method as disclosed in Japanese Patent First Publication No. 19694/1977, C.A., 87, 53269x) and benzyl anthranilate (3.4 g, 0.015 mole) are added to pyridine (25 ml), and thereto is added dicyclohexylcarbodiimide (3.1 g, 0.015 mole), and the mixture is stirred at room temperature for 72 hours. After the completion of the reaction, water (10 ml) is added to the reaction mixture, and the mixture is stirred for 30 minutes, and the undissolved materials are filtered off. The filtrate is concentrated to driness. The resulting residue is washed with ethyl acetate (100 ml) and recrystallized from water to give N-(o-benzyloxycarbonylphenyl)-trans-4-guanidinomethylcyclohexanecarboxamide hydrochloride (3.2 g) as white crystals. m.p. 93°-95° C.

Quelle