[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:14])[O:12][CH3:13])=[C:6]([CH3:15])[CH:5]=1.[F:16][C:17]1[CH:31]=[CH:30][C:20]2[N:21]=[C:22]([CH2:24]OS(C)(=O)=O)[S:23][C:19]=2[CH:18]=1.[Cl-].[NH4+]>CN(C)C=O>[F:16][C:17]1[CH:31]=[CH:30][C:20]2[N:21]=[C:22]([CH2:24][O:3][C:4]3[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:14])[O:12][CH3:13])=[C:6]([CH3:15])[CH:5]=3)[S:23][C:19]=2[CH:18]=1
15.2 mg of sodium hydride (as a 60% w/w dispersion in mineral oil) were added to a solution of 62.6 mg of methyl N-(4-hydroxy-2-methylphenyl)carbamate [prepared as described in step (a) above] in 4 ml of dimethylformamide with cooling in an ice-water bath. The resulting mixture was stirred at the same temperature for 10 minutes, and then 100.0 mg of 6-fluoro-2-methanesulfonyloxymethylbenzothiazole [prepared as described in Example 5(c)] were added to the reaction mixture. The temperature of the resulting mixture was elevated to room temperature and the mixture was stirred for 3 hours. At the end of this time a saturated aqueous ammonium chloride solution was added to the reaction mixture and the resulting mixture was extracted with ethyl acetate. The resulting extract was washed with water and then dried over anhydrous sodium sulfate. The solvent was then removed by evaporation under reduced pressure to give a crude crystalline product which was purified by column chromatography through silica gel using a 3:1 by volume mixture of hexane and ethyl acetate as the eluent, to give a crystalline solid which was washed with diethyl ether and then dried in vacuo to give 41.4 mg (yield 35%) of the title compound as a solid having a melting point of 149°-151° C.
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