Fujisawa Pharmaceutical Company, Ltd.

Kazuhiko Yoshida

Hideo Yagi

Hisae Haruta

Kazuo Kariyone

Kazuo Nakanishi

Takashi Iwata

Akira Hashimoto Nee Matui

This invention relates to a process of resolving D and L-2-(4-hydroxyphenyl) glycine. DL-2-(4-hydroxyphenyl) glycine is treated with d-3-bromo-2-oxo-10-bornanesulfonic acid to form a mixture of d-3-bromo-2-oxo-10-bornanesulfonic acid salts of D- and L-2-(4-Hydroxyphenyl) glycine. This mixture is treated with a solvent selected from the group consisting of isobutyl alcohol, a mixture of a lower alkanol and chloroform, or a mixture of a lower alkanol and toluene. The precipitate containing the d-3-bromo-2-oxo-10 bornanesulfonic acid salt of L-2-(4-hydroxyphenyl) glycine is collected. The corresponding acid salt of D-2-(hydroxyphenyl) glycine is collected from the mother liquor. D- and L-2-(4-hydroxyphenyl) glycine are then recovered by conventional means.

Process for the optical resolution of DL-2-(4-hydroxyphenyl)glycine

A quaternary ammonium salt of the formula: ##SPC1## ##EQU1## wherein A is a lower alkylene, a lower alkenylene or a lower alkadienylene; R.sub.1 and R.sub.2 are each lower alkyl which may be linked together directly or by an oxygen atom to form a saturated heterocyclic group; R.sub.3 is a lower alkyl, a halo (lower) alkyl, a lower alkynyl, phenyl (lower) alkyl which may have one or more halogen atoms as substituents on the phenyl ring, a lower alkenyl, a hydroxy (lower) alkyl, a carboxy (lower) alkyl or a lower alkenyloxycarbonyl (lower) alkyl; R.sub.4, R.sub.5 and R.sub.6 are each lower alkyl having 1 to 3 carbon atoms; X is an acid residue; and wherein the cyclohexyl ring may have one double bond, with the proviso that when the cyclohexyl ring has one double bond in the 1,2 position, A may not be ##EQU2## when X.sup.- is iodide, R.sub.4, R.sub.5 and R.sub.6 are all methyl; R.sub.1, R.sub.2 and R.sub.3 are all methyl or all ethyl, or R.sub.1 is methyl, R.sub.2 is ethyl and R.sub.3 is phenylisopropyl or isoamyl with the further proviso that when the double bond in the cyclohexyl ring is in the 2,3 position, A may not be ##EQU3## when X.sup.- is iodide, and R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are all methyl.

Quaternary ammonium salts

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Osaka, Japan

Kazuhiko Yoshida