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Preparation and isolation of 2‐methylamino‐3‐phenylpropanoic acid enantiomers using selective crystallization
Author(s) -
Shiraiwa Tadashi,
Ohta Atsushi,
Miyazaki Hideya,
Gogun Yasuhiro,
Kurokawa Hidemoto
Publication year - 1997
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/(sici)1520-636x(1997)9:4<386::aid-chir12>3.0.co;2-j
Subject(s) - chemistry , diastereomer , methylamine , mandelic acid , enantiomer , chirality (physics) , optically active , enantiomeric excess , yield (engineering) , recrystallization (geology) , propanoic acid , crystallization , stereochemistry , chiral resolution , medicinal chemistry , organic chemistry , enantioselective synthesis , catalysis , paleontology , chiral symmetry breaking , physics , materials science , quantum mechanics , nambu–jona lasinio model , metallurgy , biology , quark
First, ( RS )‐2‐chloro‐3‐phenylpropanoic acid [( RS )‐CPP] was optically resolved using ethyl ( S )‐phenylalaninate as a resolving agent, aiming at preparation of optically active 2‐methylamino‐3‐phenylpropanoic acid (MPP). The ( R )‐CPP obtained as the sodium salt monohydrate was reacted with methylamine to give ( S )‐2‐methylamino‐3‐phenylpropanoic acid [( S )‐MPP]. Next, the optical resolution of ( RS )‐MPP was also attempted via molecular compound formation with optically active mandelic acid (MAN). The molecular compound of ( R )‐MPP with ( S )‐MAN [( R )‐MPP ( S )‐MAN] was obtained as the less soluble diastereomeric compound, while the ( S )‐MPP ( S )‐MAN compound was found to be the more soluble one. Recrystallization of ( R )‐MPP ( S )‐MAN compound from water, followed by treatment with acetone, gave optically pure ( R )‐MPP in 79% yield, based on a half amount of the starting ( RS )‐MPP. The ( S )‐MPP obtained from ( S )‐MPP ( S )‐MAN compound was again subjected to formation of molecular compound with ( R )‐MAN to give optically pure ( S ,)‐MPP in 66% yield. Chirality 9:386–389, 1997. © 1997 Wiley‐Liss, Inc.