[NH:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=2)=[N:2]1.C(=O)([O-])[O-].[K+].[K+].[CH2:19]([O:26][C:27]([NH:29][CH2:30][CH2:31]OS(C)(=O)=O)=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CS(C)=O>[CH2:19]([O:26][C:27](=[O:28])[NH:29][CH2:30][CH2:31][O:12][C:9]1[CH:10]=[CH:11][C:6]([C:3]2[CH:4]=[CH:5][NH:1][N:2]=2)=[CH:7][CH:8]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1A round-bottomed flask was charged with 4-pyrazol-3-yl-phenol (840 mg, 5.25 mmol), potassium carbonate (2.17 g, 15.7 mmol), and methanesulfonic acid 2-benzyloxycarbonylamino-ethyl ester (C. A. Townsend, et al., Tetrahedron, 47, 2591 (1991)) (2.86 g, 10.5 mmol) in 10.5 ml of dry dimethylsulfoxide. The resulting solution was heated to about 70° C. for about four days. The reaction mixture was then poured into 1 N HCL, and the aqueous phase was extracted twice with ethyl acetate. The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude material was purified by column chromatography (methylene chloride to 2% methanol/methylene chloride) to afford 1.09 g (61% yield) of desired product. LRMS ([M+H+])=338.1.
Wird geladen…
