Dimethyl Ether → Oxaprozin

Participants

Reaction Steps

Rf 0.50 silica gel 60 F254 chloroform:methylisobutylketone:acetic acid 50:50:1 A mixed melting point run with an authentic sample of the methyl ether of 4-(4-hydroxyphenyl)-5-phenyl-2-oxazolepropanoic acid (obtained from the metabolite of oxaprozin as disclosed by Janssen et al., Drug Metabolism and Disposition, 6, 495 (1978)), gave m.p. 92°-108° C., clearly demonstrating the lack of identity with the known metabolite. This, coupled with the identity of the 4'-methoxybenzoin starting material characterized the methyl ether as 5-(4-methoxy)-4-phenyl-2-oxazolepropanoic acid.

Provenance & Evidence