A facile method for the production of D-p-hydroxyphenylglycine. Asymmetric transformation of DL-p-hydroxyphenylglycine using (+)-1-phenylethanesulfonic acid.

概要

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A practical method for the production of D-p-hydroxyphenylglycine, useful as a starting material for preparing semisynthetic penicillins or cephalosporins, has been developed. The diastereomeric salts of DL-p-hydroxyphenylglycine with (+)-1-phenylethanesulfonic acid as a resolving agent, were efficiently resolved into less soluble D-p-hydroxyphenylglycine (+)-1-phenylethanesulfonate [D-HPG·(+)-PES] and soluble L-HPG·(+)-PES by the fractional crystallization of its salts in aqueous solution. The soluble L-HPG·(+)-PES could be easily epimerized into DL-HPG·(+)-PES by heating it with water containing a 0.1 molar equivalent of free DL-HPG in an autoclave. When the fractional crystallization of DL-HPG with (+)-PES was simultaneously carried out under the epimerizing conditions, the DL-HPG·(+)-PES was transformed into D-HPG·(+)-PES in up to 90% yield. The present asymmetric transformation should be a suitable method for preparing D-HPG in a large scale.
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