著者

三塩 晋作 廣瀬 徹 中野 純次 松本 純一

出版者

公益社団法人 日本薬学会

雑誌

YAKUGAKU ZASSHI (ISSN:00316903)

巻号頁・発行日

vol.107, no.8, pp.634-639, 1987-08-25 (Released:2008-05-30)

参考文献数

6

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A mode of the alkaline and acidic degradation of sodium 6-[D-2-(2-(4-formyl-1-piperazinyl)-5, 8-dihydro-5-oxopyrido [2, 3-d] pyrimidine-6-carboxamido)-p-hydroxyphenylacetamido] penicillanate (1, PL-385) and structures of the degradation products were studied. Treatment of 1 with three equimolar amounts of sodium hydroxide produced a kinetically stable intermediate, (5R)-penicilloic acid (2a), which on kept at 37°C for 65h was converted into a thermodynamically stable product, (5S)-penicilloic acid (2b). Treatment of 1 with an excess of sodium hydroxide gave a deformyl derivative (3) arising from the elimination of formly group via 2. On the acidic treatment of 1, the degradation product, (5R, S)-penilloic acid (4), was yielded.