Immediate deamination from the aminomethyl group attached to 1,2-dihydropyrazin-2-one derivative during catalytic hydrogenation

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 produc...

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Bibliographic Details
Published in:Tetrahedron letters 2002-11, Vol.43 (45), p.8137-8139
Main Authors: Okada, Yoshio, Fujisawa, Yutaka, Morishita, Akihisa, Shiotani, Kimitaka, Miyazaki, Anna, Fujita, Yoshio, Li, Tingyou, Tsuda, Yuko, Yokoi, Toshio, Bryant, Sharon D., Lazarus, Lawrence H.
Format: Article
Language:English
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Summary: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. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(02)01944-5