(+-)-Methionine → 4-(1,2-Oxazol-4-yl)phenol
Reaction equation
NC(C(O)=O)CCSC.C[O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:19]=[N:20][O:21][CH:22]=2)=[CH:14][CH:13]=1.CS(O)(=O)=O>>[O:21]1[CH:22]=[C:18]([C:15]2[CH:14]=[CH:13][C:12]([OH:11])=[CH:17][CH:16]=2)[CH:19]=[N:20]1Participants
4
Conditions
- Temperature
- 70 °C
Procedure
To a round-bottomed flask was added D,L-methionine (1.30 g, 8.73 mmol), 4-(4-methoxy-phenyl)-isoxazole (1.02 g, 5.82 mmol), and methanesulfonic acid (24 ml). The resulting solution was heated to about 70° C. for about eighteen hours, and was then allowed to cool to room temperature and poured onto ice water. The mixture was adjusted to about pH 4, and the heterogenous mixture was filtered. The solid was washed with water and then dried to yield the title compound as an off-white solid (640 mg, 68% yield). LRMS ([M−H]−)=160.0.