4-Hydroxyphenylglycine → Oxfenicine

Participants

Reaction Steps

A mixture of DL-2-(4-hydroxyphenyl)glycine (10 g.), d-3-bromo-2-oxo-10-bornanesulfonic acid (20 g.) and hot 99% ethanol (100 ml.) was filtered, and the filtrate was concentrated under reduced pressure to a total weight of 40 g. Chloroform (265 g.) was added to the solution, and the solution was seeded with the authentic specimen of d-3-bromo-2-oxo-10-bornanesulfonic acid salt of L-2-(4-hydroxyphenyl)glycine and allowed to stand for 2 hours at room temperature. The precipitating crystals were collected by filtration, washed with a mixture of ethanol and chloroform (5 : 1) and dried for 12 hours at room temperature under reduced pressure to give the solvate (16.1 g.) of d-3-bromo-2-oxo-10-bronanesulfonic acid salt of L-2-(4-hydroxyphenyl)glycine with chloroform. Recrystallization from a mixture of ethanol (20 g.) and chloroform (250 g.) in a similar manner to the above gave the pure solvate (15.1 g.), m.p. 190° to 197° C. The differential thermal analysis of this solvate gave the endothermic peak at 155° to 156° C.

Provenance & Evidence