[CH:1]1([NH:4][C:5]2[S:6][CH:7]=[C:8]([C:10]3[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][CH:11]=3)[N:9]=2)[CH2:3][CH2:2]1.CI.[C:21](=O)([O-])[O-].[K+].[K+].[Li+].[OH-].Cl>CN(C=O)C.CO.C1COCC1>[CH:1]1([N:4]([CH3:21])[C:5]2[S:6][CH:7]=[C:8]([C:10]3[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][CH:11]=3)[N:9]=2)[CH2:3][CH2:2]14-(2-Cyclopropylamino-thiazol-4-yl)benzoic acid (1.98 mmol), methyliodide (4.36 mmol) and potassium carbonate were mixed in DMF (20 mL) and stirred for 72 hours at room temperature. The mixture was concentrated to dryness and partitioned between dichloromethane and water. The organic layer was dried (MgSO4) and concentrated to dryness. This solid was mixed with THF (4 mL), methanol (2 mL) and 1N LiOH (3 mmol) and heated to 50° C. for 1 hour. The mixture was then cooled to room temperature and 1N HCl was added until pH 4. The mixture was concentrated in vacuo, then the obtained residue was redissolved in dichloromethane-methanol and concentrated onto silica. Flash chromatography of the residue (silica gel, dichloromethane-methanol) gave the title compound as an off-white solid (0.1 g), m/z=275.0 in MS ES+, which was characterised by hplc and MS.
Wird geladen…
