Author/Authors :
Okada، نويسنده , , Yoshio and Fujisawa، نويسنده , , Yutaka and Morishita، نويسنده , , Akihisa and Shiotani، نويسنده , , Kimitaka and Miyazaki، نويسنده , , Anna and Fujita، نويسنده , , Yoshio and Li، نويسنده , , Tingyou and Tsuda، نويسنده , , Yuko and Yokoi، نويسنده , , Toshio and Bryant، نويسنده , , Sharon D. and Lazarus، نويسنده , , Lawrence H.، نويسنده ,
Abstract :
The catalytic hydrogenation of 3,6-bis(benzyloxycarbonylaminomethyl)-5-methyl-1,2-dihydropyrazin-2-one to remove benzyloxycarbonyl (Z) groups resulted in a side reaction. Purification by reverse-phase HPLC and analysis by proton nuclear magnetic resonance (1H NMR) spectroscopy identified the product as 3-aminomethyl-5,6-dimethyl-1,2-dihydropyrazin-2-one. It was determined through the synthesis of two 1,2-dihydropyrazin-2-one derivatives, composed of alanine and 2,3-diaminopropionic acid that deamination occurred specifically and easily (under atmospheric pressure and at the room temperature) only in the case of 6-benzyloxycarbonylaminomethyl-3,5-dimethyl-1,2-dihydropyrazin-2-one. The catalytic hydrogenation of 3,6-bis(benzyloxycarbonylaminomethyl)-5-methyl-1,2-dihydropyrazin-2-one specifically yields the deaminated product, 3-aminomethyl-5,6-dimethyl-1,2-dihydropyrazin-2-one.
