ペニシリンに関する合成研究 (第2報)
ペニロアルデハイドの合成
1950 年 70 巻 6 号 p. 344-346
詳細
1950 年 70 巻 6 号 p. 344-346
As a part of penicillin synthesis, penilloaldehyde-G and carbethoxypenilloaldehyde-X were synthesized.
Needle crystals of penilloaldehyde-G acetal, m.p. 40-41°, were obtained from phenylacetic chloride and aminoacetal. The former was saponified with 10% sulfuric acid to penilloaldehyde-G, m.p. 111-114°, which gave yellow needles of 2, 4-dinitrophenylhydrazone, decompn. 198°.
Needle crystals of acid chloride, m.p. 43°, was obtained from p-hydroxyphenylacetic acid through p-carbethoxyhydroxyphenylacetic acid, prisms, m.p. 87-88°. Condensation of the former with aminoacetal gave white needles of the acetal of carbethoxypenilloaldehyde-X, m.p. 83-84°. Saponification of this acetal with 10% sulfuric acid gave carbethoxypenilloaldehyde-X, white needles containing 1/2mol. water of crystallization, m.p. 86-88°. In this reaction, the carbethoxy radical in the p-position could not be liberated so that the objective penilloaldehyde-X could not be obtained. 2, 4-Dinitrophenylhydrazone of carbethoxypenilloaldehyde-X is yellow needles of decompn. 192°.
