938-97-6Relevant articles and documents
The Optical Resolution and Asymmetric Transformation of DL-p-Hydroxyphenylglycine with (+)-1-Phenylethanesulfonic Acid
Yoshioka, Ryuzo,Tohyama, Masanori,Ohtsuki, Osamu,Yamada, Shigeki,Chibata, Ichiro
, p. 649 - 652 (2007/10/02)
Optically active 1-phenylethanesulfonic acid was found to be an efficient resolving agent for the optical resolution and asymmetric transformation of DL-p-hydroxyphenylglycine.When DL-p-hydroxyphenylglycine was resolved by the fractional crystallization of its diastereomeric salt with (+)-1-phenylethanesulfonic acid, less soluble D-p-hydroxyphenylglycine (+)-1-phenylethanesulfonate was obtained in a good yield.Soluble L-HPG*(+)-PES was easily epimerized into DL-HPG*(+)-PES by heating it at 100 deg C in glacial acetic acid in the presence of a small amount of salicylaldehyde.Under such epimerizing conditions, the asymmetric transformation of DL-HPG*(+)-PES was attempted by simultaneously combining the fractional crystallization of the less soluble D-HPG*(+)-PES and the epimerization of the soluble L-HPG*(+)-PES.This asymmetric tranformation was achieved succesfully; that is, 80percent of the DL-HPG used as the starting material was converted into D-HPG.