(+-)-Methionine → 4-(1,2-Oxazol-4-yl)phenol

反応式

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]1

参加物

反応物 3

HCID 876(+-)-Methionine

HCID 6395Methanesulfonic Acid

HCID 185236724-(4-Methoxyphenyl)-1,2-oxazole

生成物 1

HCID 185236244-(1,2-Oxazol-4-yl)phenol収率 68.2%

反応条件

温度: 70 °C

実験手順

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.