[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]1[NH:8][C:9](=O)[CH2:10][CH:11]2[CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]=12.[Cl-].[NH4+].[F:23][C:24]([F:35])([F:34])[C:25]1[CH:30]=[CH:29][C:28]([N:31]=[C:32]=[O:33])=[CH:27][CH:26]=1>C1COCC1>[F:23][C:24]([F:34])([F:35])[C:25]1[CH:26]=[CH:27][C:28]([NH:31][C:32]([N:8]2[CH2:9][CH2:10][CH:11]3[CH2:19][C:18]4[C:13]([C:12]3=[N:7]2)=[CH:14][CH:15]=[CH:16][CH:17]=4)=[O:33])=[CH:29][CH:30]=1To a solution of 0.204 g (0.0053 mol) of lithium aluminum hydride suspended in 20 mL THF was added dropwise 1.0 g (0.0053 mol) of the product from step C dissolved in 10 mL THF. The dark reaction mixture was refluxed for 1 hour, cooled to 0° C. and 50 mL of a saturated solution of ammonium chloride was added. The reaction was extracted with ethyl acetate (3×50 mL), washed with brine (1×100 mL), dried over anhydrous magnesium sulfate, filtered into a flask and added 1.0 g (0.0053 mol) α,α,α-trifluoro-p-tolylisocyanate all at once. The reaction was stirred for 0.5 hours, concentrated under vacuum and chromatographed using 30% ethyl acetate/70% hexanes as eluent to afford 0.250 g of a purple solid, mp 136°-138° C.
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