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Preparation of d p hydroxyphenyl glycine optical resolution of dl p hydroxyphenyl glycine by preferential crystallization procedure


Agricultural and Biological Chemistry 42(8): 1521-1526
Preparation of d p hydroxyphenyl glycine optical resolution of dl p hydroxyphenyl glycine by preferential crystallization procedure
Optical resolution of DL-p-hydroxyphenylglycine was studied in order to develop a practical method for the production of D-p-hydroxyphenylglycine useful as a starting material for preparing semisynthetic penicillins and cephalosporins. Among the various aromatic sulfonates of DL-p-hydroxyphenylglycine, the benzenesulfonate, the o-toluenesulfonate, the p-toluenesulfonate, the p-ethylbenzenesulfonate, the sulfosalicylate and the 2-naphthol-6-sulfonate were easily resolved by a preferential crystallization procedure. The optically pure sulfonates of D-p-hydroxyphenylglycine were obtained in good yield and were easily converted to optically pure D-p-hydroxyphenylglycine without racemization. The undesired sulfonates of the L-isomer were readily racemized and could be reused for the resolution step. Industrial production of D-p-hydroxyphenylglycine by the present simple resolution method is considered to be very promising.


Accession: 006173013



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