Facile synthesis of optically pure (S)-3-p-hydroxyphenyllactic acid derivatives.
Optically pure (S)-3-p-hydroxyphenyllactic acid derivatives are important intermediates of peroxisome proliferator-activated receptor alpha/gamma dual agonists and heteropeptides. Many efforts have been made for synthesis of those intermediates, but there exist some flaws yet. We observed that dielectric constants of organic solvents drastically affected diazotization of O-benzyl-L-tyrosine. Optically pure (S)-3-p-benzyloxyphenyllactic acid was obtained by simple recrystallization when DMF or DMSO of higher dielectric constant was used as a co-solvent in diazotization of O-benzyl-L-tyrosine. It was easily turned into various optically pure (S)-3-p-hydroxyphenyllactic acid derivatives.
Zeng
Q L
QL
Key Laboratory for Chemical Biology of the Province of Fujian, Department of Chemistry, Xiamen University, Xiamen, China. qlzeng@cdut.edu.cn
Wang
H Q
HQ
Liu
Z R
ZR
Li
B G
BG
Zhao
Y F
YF
D008968:Molecular Conformation; D010666:Phenylpropionates / Q000138:chemical synthesis / Q000737:chemistry; D012997:Solvents
D010666:Phenylpropionates; D012997:Solvents; C001418:4-hydroxyphenyllactic acid