Dimethyl Ether → Oxaprozin
Reaction equation
COC.O[C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[C:13]([CH2:22][CH2:23][C:24]([OH:26])=[O:25])[O:14][C:15]=2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:7][CH:6]=1>C(Cl)(Cl)Cl.CC(CC(C)C)=O.C(O)(=O)C>[CH:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[C:13]([CH2:22][CH2:23][C:24]([OH:26])=[O:25])[O:14][C:15]=2[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:7][CH:6]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
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.