Optical resolution by preferential crystallization of (RS)-2-benzoylamino-2-benzyl-3-hydroxypropanoic acid and its use in synthesizing optically active 2-amino-2- …

T Shiraiwa, M Suzuki, Y Sakai, H Nagasawa…

Index: Shiraiwa, Tadashi; Suzuki, Masahiro; Sakai, Yoshio; Nagasawa, Hisashi; Takatani, Kazuhiro; Noshi, Daisuke; Yamanashi, Kenji Chemical and pharmaceutical bulletin, 2002 , vol. 50, # 10 p. 1362 - 1366

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Citation Number: 11

Abstract

To synthesize optically active 2-amino-2-methyl-3-phenylpropanoic acid (1),(RS)-2- benzoylamino-2-benzyl-3-hydroxypropanoic acid [(RS)-2] was first optically resolved using cinchonidine as a resolving agent to yield optically pure (S)-and (R)-2 in yields of about 70%, based on half of the starting amount of (RS)-2. Next, the racemic structure of (RS)-2 was examined based on melting point, solubility, IR spectrum, and binary and ternary ...