p-Hydroxyphenylglycine..alpha.-phenylethanesulfonate, process fo

Details p-Hydroxyphenylglycine..alpha.-phenylethanesulfonate, process fo p-Hydroxyphenylglycine..alpha.-phenylethanesulfonate, process fo

1982-09-09

1983-11-15

Reamer, James H.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260505P, 562401, C07C14326

Patent

active

044155042

ABSTRACT:
p-Hydroxyphenylglycine..alpha.-phenylethanesulfonate which is useful for the production of optically active p-hydroxyphenylglycine and optically active .alpha.-phenylethanesulfonic acid is disclosed. p-Hydroxyphenylglycine..alpha.-phenylethanesulfonate is produced by either reacting DL-p-hydroxyphenylglycine with optically active .alpha.-phenylethanesulfonic acid or reacting (.+-.)-.alpha.-phentylethanesulfonic acid with optically active p-hydroxyphenylglycine to form two diastereomers of DL-p-hydroxyphenylglycine optically active .alpha.-phenylethanesulfonate or optically active p-hydroxyphenylglycine (.+-.)-.alpha.-phenylethanesulfonate, and isolating one diastereomer according to the difference between solubilities of the diastereomers, optionally, combining selective crystallization of one diastereomer and epimerization of another diastereomer in the case of reaction of DL-p-hydroxyphenylglycine and optically active .alpha.-phenylethanesulfonic acid. This reaction is utilized in the resolution of p-hydroxyphenylglycine or .alpha.-phenylethanesulfonic acid by deacidifying the resulting diastereomer.

REFERENCES:
patent: 3933902 (1976-01-01), Watanabe et al.
patent: 3994962 (1976-11-01), Shirai et al.
patent: 4016205 (1977-04-01), Kariyone et al.
patent: 4115439 (1978-09-01), Aoki et al.
patent: 4233456 (1980-11-01), Schmand et al.
patent: 4309362 (1982-01-01), Chibata et al.
Yamada et al., Chem. Abst., vol. 90, #138,159y (1979).

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