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Preparation of (2S,4R)‐2,4‐thiazolidinedicarboxylic acid by separation of diastereoisomeric salts with organic amines
Author(s) -
Shiraiwa Tadashi,
Kaito Takehiro,
Katayama Takashi,
Ikeda Tomoko,
Ishikawa Joji,
Kurokawa Hidemoto
Publication year - 1999
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(1999)11:4<326::aid-chir11>3.0.co;2-2
Subject(s) - chemistry , diastereomer , benzylamine , propylamine , acetic acid , salt (chemistry) , yield (engineering) , organic chemistry , chirality (physics) , glyoxylic acid , imine , medicinal chemistry , stereochemistry , amine gas treating , catalysis , materials science , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , metallurgy , quark
L ‐Cysteine was condensed with glyoxylic acid monohydrate in acetic acid at 30°C to give (4R)‐2,4‐thiazolidinedicarboxylic acid [(4R)‐TDA] as a mixture of two diastereoisomers, (2R,4R)‐ and (2S,4R)‐TDA. An attempt was made to separate (2S,4R)‐TDA from the diastereoisomeric salts of (4R)‐TDA with 1‐propylamine, 2‐methyl‐2‐propylamine, benzylamine, and (R)‐ and (S)‐1‐phenylethylamines [(R)‐ and (S)‐PEA]. The salts of (2S,4R)‐TDA were preferentially crystallized as less soluble diastereoisomeric salts. When the salt with (R)‐PEA was employed, the separation was successfully achieved to afford optically pure (2S,4R)‐TDA in a yield of 41%, based on the starting amount of the diastereoisomeric mixture of (4R)‐TDA. Chirality 11:326–329, 1999. © 1999 Wiley‐Liss, Inc.