[C:1]([OH:5])(=O)[CH2:2][OH:3].N1C=CC=CC=1.C[Si](Cl)(C)C.C(Cl)(=O)C(Cl)=O.[F:23][C:24]1[CH:37]=[CH:36][C:27]([CH2:28][N:29]2[CH2:34][CH2:33][NH:32][C@H:31]([CH3:35])[CH2:30]2)=[CH:26][CH:25]=1.Cl>CN(C)C1C=CN=CC=1.ClCCl.CN(C)C=O>[F:23][C:24]1[CH:37]=[CH:36][C:27]([CH2:28][N:29]2[CH2:34][CH2:33][N:32]([C:1](=[O:5])[CH2:2][OH:3])[C@H:31]([CH3:35])[CH2:30]2)=[CH:26][CH:25]=1To a solution of glycolic acid (0.70 g, 9.2 mmol), 4-dimethylaminopyridine (catalytic) and pyridine (1.52 mL, 18.6 mmol) in dry dichloromethane (20 mL) was added trimethylsilylchloride (2.39 mL, 2.05 mmol) dropwise. The reaction was stirred at ambient temperature for 4 hours. The reaction was then cooled to 0° C. and catalytic dimethylformamide (3 drops) was added followed by addition of oxalyl chloride. The reaction was stirred at 0° C. for one hour and then 30 minutes at ambient temperature. The reaction was cooled back to 0° C. and (3R)-1-(4-fluoro-benzyl)-3-methyl-piperazine (2.11 g, 10.12 mmol) was added as a solution in pyridine (2.45 mL, 30.4 mmol). The reaction was allowed to warm to ambient temperature and stirred for 2 hours. The reaction was neutralized with 1N hydrochloric acid and extracted with dichloromethane (2×). The organic layers were combined, dried over magnesium sulfate, filtered and concentrated in vacuo. Chromatography on silica gel gave the title compound (1.84 g).
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