SYNTHESIS OF BETA-(4-PYRIDYL)-DL-ALANINE AND OF BETA-(4-PYRIDYL-1-OXIDE)-DL-ALANINE,D-ALANINE, AND L-ALANINE
SYNTHESIS OF BETA-(4-PYRIDYL)-DL-ALANINE AND OF BETA-(4-PYRIDYL-1-OXIDE)-DL-ALANINE,D-ALANINE, AND L-ALANINE
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DOI：
10.1021/jo01098a020
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发表时间：
1958-01-01
影响因子：
3.6
通讯作者：
NIEMANN, C
中科院分区：
文献类型：
--
作者：
BIXLER, RL;NIEMANN, C
本文报道了一种实用的合成方法--β-（4-吡啶基）-DL-丙氨酸的方法，该方法适合于克级规模的应用。本文报道了以较好的收率合成3-（4-吡啶基-1-氧化物）-DL-丙氨酸的方法，并对Ar-苯甲酰基-β-（4-吡啶基-1-氧化物）-DL-丙氨酸进行了满意的拆分。第一个3基于序列4-吡啶基甲醇-> 4-吡啶基甲基溴-n-苯甲酰氨基-（4-吡啶基甲基）丙二酸二乙酯-> 3-（4-吡啶基）-DL-丙氨酸，第二个4基于序列4-甲基吡啶-> α-肟基-> 3-（4-吡啶基）丙酸乙酯-> α-肟基-> 3-（4-吡啶基）丙酸-> β-（4-吡啶基）丙酸->（4-吡啶基）-DL-丙氨酸。这两种合成都涉及一个步骤，其中获得的产率很低。丙二酸酯缩合的产率仅为4%，克莱森缩合的产率为12%。因此决定研究丙二酸酯的缩合反应，以提高产率。
A practical synthesis of ß-(4-pyridyl)-DL-alanine, suitable for application on a gram scale, has beendeveloped./3-(4-Pyridyl-l-oxide)-DL-alanine has been prepared in good yield, by a procedure capable of being employed on a much larger scale, and a satisfactory resolution of Ar-benzoyl-/3-(4-pyridyl-l-oxide)-DL-alanine has been achieved.Two methods have been reported for the syn-thesis of ß-(4-pyridyl)-DL-alanine. The first3 was based uponthe sequence, 4-pyridylcarbinol-> 4-pyridylmethyl bromide—«-diethyl benzamido-(4-pyridylmethyl) malonate-»-/3-(4-pyridyl)-DL-alanine and the second4 upon the sequence, 4-picoline-* ethyl a-oximino-/3-(4-pyridyl) propionate—* a-ox-imino-/3-(4-pyridyl) propionic acid-*/?-(4-pyridyl)-DL-alanine. Both syntheses involved a step in which poor yields were obtained. The malonic ester con-densation gave but a 4% yield, and the Claisen condensation a 12% yield. It ivas decided to study the malonic ester condensation with theaim of improving the yield.